Substituted 2-(het)arylimidazolylcarboxyamides as pesticides

ABSTRACT

The present invention relates to compounds of the general formula (I) 
                         
in which Q, V, T, W, X, Y and A have the meanings given in the description—and to their use for controlling animal pests.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a divisional of U.S. application Ser. No.16/076,786, filed Aug. 9, 2018, which is a National Stage entry ofInternational Application No. PCT/EP2017/052501, and claims priorityfrom European Patent Application No. 16155132.0, filed Feb. 11, 2016,the content of each of these applications is herein incorporated byreference in their entirety.

BACKGROUND Field

The present application relates to novel heterocyclic compounds, tointermediates for their preparation and their use for controlling animalpests.

WO 2011/009804 A2 describes heterocyclic compounds including, interalia, imidazolylcarboxamides which can be used as insecticides. However,imidazolylcarboxamides directly substituted at the imidazolyl radical byaryls or hetaryls are not described. The imidazolylcarboxamides listedin WO 2011/009804 A2 have considerable weaknesses in their insecticidalaction.

Modern insecticides have to meet many demands, for example in relationto extent, persistence and spectrum of their action and possible use.Questions of toxicity, sparing of beneficial species and pollinators,environmental properties, application rates, combinability with otheractive compounds or formulation auxiliaries play a role, as does thequestion of the effort required for the synthesis of an active compound;furthermore, resistances may occur, to mention only some parameters. Forall these reasons alone, the search for novel crop protectioncompositions cannot be considered complete, and there is a constant needfor novel compounds having improved properties compared to the knowncompounds, at least in relation to individual aspects.

SUMMARY

It was an object of the present invention to provide compounds whichwiden the spectrum of the pesticides in various aspects.

This object, and further objects which are not stated explicitly whichcan be discerned or derived from the connections discussed herein, areachieved by the provision of compounds of the formula (I)

in which (configuration (0))

-   Q represents oxygen or sulphur,-   V represents a radical from the group consisting of hydrogen,    halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and cyano,-   W represents a radical from the group consisting of hydrogen,    halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and cyano,-   X represents a radical from the group consisting of optionally    substituted aryl or hetaryl, Y represents a radical from the group    consisting of hydrogen, cyano, optionally substituted alkyl, alkenyl    or alkynyl, cycloalkyl, optionally interrupted by heteroatoms and    optionally substituted, and cycloalkylalkyl, arylalkyl or    hetarylalkyl, optionally interrupted by heteroatoms and optionally    substituted,-   A represents a radical from the group consisting of hydrogen,    optionally substituted alkyl, alkenyl or alkynyl and cycloalkyl or    cycloalkylalkyl, optionally interrupted by heteroatoms and    optionally substituted,-   T represents oxygen or an electron pair,-   and salts thereof.

For the radical X the term substituted aryl or hetaryl also includesradicals which have, attached to two adjacent ring positions of the arylor hetaryl ring, a chain consisting of one to two heteroatoms from thegroup consisting of S, N and O and/or one to five carbon atoms, thusforming an optionally partially unsaturated aliphatic, aromatic,heteroaromatic or optionally partially unsaturated heterocyclic ring,such that for X together with the aryl or hetaryl radical a bicycleresults.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

Preferred substituents or ranges for the radicals shown in the compoundsof the formula (I) are illustrated below. The combination thereof formsthe range of preference (1-1).

-   Q represents oxygen or sulphur,-   V represents a radical from the group consisting of hydrogen,    halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy and cyano,-   W represents a radical from the group consisting of hydrogen,    halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy and cyano,-   X represents a radical from the group consisting of aryl and    hetaryl, optionally mono- to polysubstituted independently of one    another by halogen, NL¹L², nitro, cyano or optionally substituted    alkyl, haloalkyl, alkoxy, alkyl-S(O)_(m)—, haloalkoxy,    haloalkyl-S(O)_(m)—, carboxy, aryl or hetaryl,-   where-   L¹ represents a radical from the group consisting of hydrogen,    optionally substituted alkyl, alkenyl, alkynyl and cycloalkyl,-   L² represents a radical from the group consisting of hydrogen,    optionally substituted alkyl, alkenyl, alkynyl and cycloalkyl,

or

-   L¹ and L² together with N represent an optionally substituted    saturated, partially saturated or aromatic heterocycle which has 3    to 7 ring atoms and is attached via N,-   Y represents a radical from the group consisting of hydrogen,    methyl, cyano,    -   C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally mono- to        polysubstituted independently of one another by halogen,        C₁-C₄-alkoxy, C₁-C₄-alkyl-S(O), or cyano,    -   C₃-C₈-cycloalkyl, optionally mono- to disubstituted        independently of one another by halogen, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy or cyano,    -   straight-chain or branched C₃-C₈-cycloalkyl-C₁-C₄-alkyl,        optionally interrupted once to twice independently of one        another by O, S(O)_(m), CO or NR² and optionally mono- to        tetrasubstituted independently of one another by halogen,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or cyano, and    -   arylalkyl or hetarylalkyl, optionally mono- to trisubstituted        independently of one another by halogen, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkyl-S(O)_(m)—,        C₁-C₄-haloalkoxy, C₁-C₄-haloalkyl-S(O)_(m)—, nitro or cyano,-   m represents a number 0, 1 or 2,-   A represents a radical from the group consisting of hydrogen,    methyl,    -   C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally mono- to        polysubstituted independently of one another by halogen,        C₁-C₄-alkoxy, C₁-C₄-alkyl-S(O)_(m), or cyano and    -   C₃-C₆-cycloalkyl, optionally mono- to disubstituted        independently of one another by halogen, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy or cyano and    -   straight-chain or branched C₃-C₈-cycloalkyl-C₁-C₄-alkyl,        optionally mono- to disubstituted independently of one another        by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or cyano,-   R² represents a radical from the group consisting of hydrogen,    optionally substituted alkyl, alkenyl, alkynyl and cycloalkyl,-   T represents oxygen or an electron pair,-   and salts thereof.

More preferred substituents or ranges for the radicals shown in thecompounds of formula (I) are illustrated below. The combination thereofforms the range of preference (1-2).

Here, the radicals Q, V, W, Y, m, A, R² and T are as defined in range ofpreference (1-1) and

-   X represents a radical from the group consisting of aryl or hetaryl,    optionally mono- to polysubstituted independently of one another by    -   halogen, NL¹L², nitro, cyano or optionally substituted alkyl,        haloalkyl, alkoxy, alkyl-S(O)_(m)—, haloalkoxy,        haloalkyl-S(O)_(m)—, carboxy, aryl or hetaryl,    -   or represents an aryl or hetaryl ring which has a chain        consisting of one to two heteroatoms from the group consisting        of N, S and O and/or one to five carbon atoms attached to two        adjacent ring positions, thus forming an optionally partially        unsaturated aliphatic, aromatic, heteroaromatic or optionally        partially unsaturated heterocyclic ring,    -   where-   L¹ represents a radical from the group consisting of hydrogen,    optionally substituted alkyl, alkenyl, alkynyl and cycloalkyl,-   L² represents a radical from the group consisting of hydrogen,    optionally substituted alkyl, alkenyl, alkynyl and cycloalkyl,    -   or-   L¹ and L² together with N represent an optionally substituted    saturated, partially saturated or aromatic heterocycle which has 3    to 7 ring atoms and is attached via N.

Particularly preferred substituents or ranges for the radicals shown inthe compounds of formula (I) are elucidated below. The combinationthereof forms the range of preference (2-1).

-   Q represents oxygen or sulphur,-   V represents a radical from the group consisting of hydrogen,    fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,    trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy    and cyano,-   W represents a radical from the group consisting of hydrogen,    fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,    trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy    and cyano,-   X represents a radical from the group consisting of aryl and    hetaryl, optionally mono- to polysubstituted independently of one    another by    -   halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,        C₁-C₄-alkyl-S(O)_(m)—, C₁-C₄-haloalkoxy,        C₁-C₄-haloalkyl-S(O)_(m)—, C₁-C₄-carboxy, NL¹L², nitro, cyano or        aryl or hetaryl, mono- to trisubstituted independently of one        another by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,        C₁-C₄-alkyl-S(O)_(m)—, C₁-C₄-haloalkoxy,        C₁-C₄-haloalkyl-S(O)_(m)—, nitro or cyano,    -   where-   L¹ represents a radical from the group consisting of hydrogen,    optionally substituted C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl or    C₃-C₆-cycloalkyl,-   L² represents a radical from the group consisting of hydrogen,    optionally substituted C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl or    C₃-C₆-cycloalkyl,    -   or-   L¹ and L² together with N represent an optionally substituted    saturated, partially saturated or aromatic heterocycle which has 3    to 7 ring atoms and is attached via N,-   Y represents a radical from the group consisting of hydrogen, cyano,    -   C₁-C₄-alkyl, C₃-C₄-alkenyl or C₃-C₄-alkynyl, optionally mono- to        pentasubstituted independently of one another by fluorine,        chlorine, bromine, methoxy, ethoxy, methyl-S(O)_(m)—,        ethyl-S(O), or cyano,    -   C₃-C₆-cycloalkyl, optionally mono- to disubstituted        independently of one another by fluorine, chlorine, bromine,        methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyano, and    -   straight-chain or branched C₃-C₆-cycloalkyl-C₁-C₂-alkyl,        optionally interrupted once to twice independently of one        another by O, S(O)_(m), CO or NR² and optionally mono- to        tetrasubstituted independently of one another by fluorine,        chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy,        ethoxy or cyano,-   m represents a number 0, 1 or 2,-   A represents a radical from the group consisting of hydrogen,    methyl,    -   C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally mono- to        pentasubstituted independently of one another by fluorine,        chlorine, bromine, methoxy, ethoxy, methyl-S(O)_(m)—,        ethyl-S(O), or cyano,    -   C₃-C₆-cycloalkyl, optionally mono- to disubstituted        independently of one another by fluorine, chlorine, bromine,        methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyano, and    -   straight-chain or branched C₃-C₆-cycloalkyl-C₁-C₂-alkyl,        optionally mono- to disubstituted independently of one another        by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,        methoxy, ethoxy or cyano,-   R² represents a radical from the group consisting of hydrogen,    optionally substituted alkyl, alkenyl, alkynyl and cycloalkyl,-   T represents oxygen or an electron pair,-   and salts thereof.

More particularly preferred substituents or ranges for the radicalsshown in the compounds of formula (I) are illustrated below. Thecombination thereof forms the range of preference (2-2).

Here, the radicals Q, V, W, Y, m, A, R² and T are as defined in range ofpreference (2-1) and

-   X represents a radical from the group consisting of    -   aryl and hetaryl, optionally mono- to polysubstituted        independently of one another by    -   halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,        C₁-C₄-alkyl-S(O)_(m)—, C₁-C₄-haloalkoxy,        C₁-C₄-haloalkyl-S(O)_(m)—, C₁-C₄-carboxy, NL¹L², nitro, cyano or        aryl or hetaryl, optionally mono- to trisubstituted        independently of one another by halogen, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkyl-S(O)_(m)—,        C₁-C₄-haloalkoxy, C₁-C₄-haloalkyl-S(O)_(m)—, nitro or cyano,        -   or represents an aryl or hetaryl ring which has a chain            consisting of one or two heteroatoms from the group            consisting of N, S and O and one or two carbon atoms            attached to two adjacent ring positions, thus forming a            heteroaromatic or optionally partially unsaturated            heterocyclic ring,    -   where-   L¹ represents a radical from the group consisting of hydrogen,    optionally substituted C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl or    C₃-C₆-cycloalkyl,-   L² represents a radical from the group consisting of hydrogen,    optionally substituted C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl or    C₃-C₆-cycloalkyl,-   or-   L¹ and L² together with N represent an optionally substituted    saturated, partially saturated or aromatic heterocycle which has 3    to 7 ring atoms and is attached via N.

Very particularly preferred substituents or ranges of the radicals shownin the compounds of the formula (I) are illustrated below. Taking intoaccount the position of the carboxamide group at the imidazole radical,the very particularly preferred structure (II) is obtained. Thecombination thereof forms the range of preference (3-1).

-   Q represents oxygen or sulphur,-   V represents a radical from the group consisting of hydrogen,    fluorine, chlorine, methyl and cyano,-   W represents a radical from the group consisting of hydrogen,    fluorine, chlorine, bromine, methyl, ethyl and cyano,-   X represents a radical from the group consisting of aryl or hetaryl,    -   optionally mono- to trisubstituted independently of one another        by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,        trifluoromethyl, methoxy, ethoxy, methyl-S(O)_(m)—,        ethyl-S(O)_(m)—, cyclopropylmethyl-S(O)_(m)—, difluoromethoxy,        trifluoromethoxy, trifluoromethyl-S(O)_(m)—,        difluoroethyl-S(O)_(m)—, trifluoroethyl-S(O)_(m)—,        (tetrahydro-2H-pyran-4-yloxy)methyl, dimethylsulphamoyl,        methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoethoxy,        (cyclopropylcarbonyl)oxy, morpholin-4-yl, dimethylamino,        diethylamino, ethylmethylamino, cyano and phenyl, naphthyl,        pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, furanyl,        thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,        pyrazolyl, imidazolyl, oxadiazolyl, thiadiazolyl,        benzofuran-2-yl or 1.2,3-triazol-4-yl, optionally mono- to        trisubstituted independently of one another by fluorine,        chlorine, bromine, methyl, ethyl, difluoromethyl,        trifluoromethyl, methoxy, ethoxy, methyl-S(O)_(m)—,        ethyl-S(O)_(m)—, cyclopropylmethyl-S(O)_(m)—, difluoromethoxy,        trifluoromethoxy, trifluoromethyl-S(O)_(m)—,        difluoroethyl-S(O)_(m)—, trifluoroethyl-S(O)_(m)—,        (tetrahydro-2H-pyran-4-yloxy)methyl, dimethylsulphamoyl,        methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoethoxy,        (cyclopropylcarbonyl)oxy, morpholin-4-yl or cyano,-   Y represents a radical from the group consisting of hydrogen, benzyl    and methyl, ethyl, propyl, allyl or propargyl, optionally mono- to    trisubstituted independently of one another by fluorine, methoxy,    ethoxy or cyano,-   m represents a number 0, 1 or 2,-   A represents a radical from the series hydrogen; methyl, ethyl,    propyl, allyl, propargyl, cyclopropyl or cyclopropylmethyl,    optionally mono- to trisubstituted independently of one another by    fluorine, methoxy, ethoxy or cyano, and-   T represents oxygen or an electron pair.

Taking into account the position of the carboxamide group at theimidazole radical, formula (I) gives the very particularly preferredstructure (II) and its salts. Very particularly preferred substituentsor ranges of the radicals shown in the compounds of the formula (II) areillustrated below. The combination thereof forms the range of preference(3-2).

Here, the radicals Q, V, W, Y, m, A and T are as defined in range ofpreference (3-1) and

-   X represents a radical from the group consisting of aryl or hetaryl,    -   optionally mono- to trisubstituted independently of one another        by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,        trifluoromethyl, methoxy, ethoxy, methyl-S(O)_(m)—,        ethyl-S(O)_(m)—, cyclopropylmethyl-S(O)_(m)—, difluoromethoxy,        trifluoromethoxy, trifluoromethyl-S(O)_(m)—,        difluoroethyl-S(O)_(m)—, trifluoroethyl-S(O)_(m)—,        (tetrahydro-2H-pyran-4-yloxy)methyl, dimethylsulphamoyl,        methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoethoxy,        (cyclopropylcarbonyl)oxy, morpholin-4-yl, dimethylamino,        diethylamino, ethylmethylamino, cyano and phenyl, naphthyl,        pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, furanyl,        thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,        pyrazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, benzofuran2-yl        or 1,2,3-triazol-4-yl, optionally mono- to trisubstituted        independently of one another by fluorine, chlorine, bromine,        methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy,        methyl-S(O)_(m)—, ethyl-S(O)_(m)—, cyclopropylmethyl-S(O)_(m)—,        difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O)_(m)—,        difluoroethyl-S(O)_(m)—, trifluoroethyl-S(O)_(m)—,        (tetrahydro-2H-pyran-4-yloxy)methyl, dimethylsulphamoyl,        methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoethoxy,        (cyclopropylcarbonyl)oxy, morpholin-4-yl or cyano,    -   or    -   represents an aryl or hetaryl ring which has a chain consisting        of one or two oxygen atoms and one or two carbon atoms attached        to two adjacent ring positions, thus forming a heteroaromatic or        optionally partially unsaturated heterocyclic ring,

Especially preferred substituents or ranges for the radicals shown inthe compounds of the formula (I) are elucidated below. Taking intoaccount the position of the carboxamide group at the imidazole radical,the especially preferred structure (II) is obtained. Its combinationwith the especially preferred substituents forms the preferred range(4-1).

-   Q represents oxygen or sulphur,-   V represents hydrogen or fluorine,-   W represents a radical from the group consisting of hydrogen,    chlorine, bromine and methyl,-   X represents a radical from the group consisting of phenyl,    naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl,    furanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,    pyrazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, benzofuran-2-yl or    1,2,3-triazol-4-yl, optionally mono- to trisubstituted independently    of one another by fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S(O)_(m)—,    ethyl-S(O)_(m)—, cyclopropylmethyl-S(O)_(m)—, difluoromethoxy,    trifluoromethoxy, trifluoromethyl-S(O)_(m)—,    difluoroethyl-S(O)_(m)—, trifluoroethyl-S(O)_(m)—,    (tetrahydro-2H-pyran-4-yloxy)methyl, dimethylsulphamoyl,    methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoethoxy,    (cyclopropylcarbonyl)oxy, morpholin-4-yl, dimethylamino,    diethylamino, ethylmethylamino, cyano and phenyl, naphthyl, pyridyl,    pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, furanyl, thienyl,    oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl,    imidazolyl, oxadiazolyl, thiadiazolyl, benzofuran-2-yl or    1,2,3-triazol-4-yl, optionally mono- to trisubstituted independently    of one another by fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S(O)_(m)—,    ethyl-S(O)_(m)—, cyclopropylmethyl-S(O)_(m)—, difluoromethoxy,    trifluoromethoxy, trifluoromethyl-S(O)_(m)—,    difluoroethyl-S(O)_(m)—, trifluoroethyl-S(O)_(m)—,    (tetrahydro2H-pyran-4-yloxy)methyl, dimethylsulphamoyl,    methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoethoxy,    (cyclopropylcarbonyl)oxy, morpholin-4-yl or cyano,-   Y represents a radical from the group consisting of hydrogen,    methyl, ethyl, propyl, difluoroethyl, trifluoroethyl, methoxymethyl,    ethoxymethyl, cyanomethyl and benzyl,-   m represents a number 0, 1 or 2,-   A represents a radical from the group consisting of hydrogen,    methyl, ethyl, propyl, difluoroethyl, trifluoroethyl, methoxymethyl,    ethoxymethyl, cyanomethyl, allyl, propargyl, cyclopropyl or    cyclopropylmethyl,-   T represents oxygen or an electron pair,-   and salts thereof.

Taking into account the position of the carboxamide group at theimidazole radical, formula (I) gives the very especially preferredstructure (II) and its salts. Especially preferred substituents orranges for the radicals shown in the compounds of the formula (II) areillustrated below. The combination thereof forms the range of preference(4-2).

Here, the radicals Q, V, W, Y, m, A and T are as defined in range ofpreference (4-1) and

-   X represents a radical from the group consisting of phenyl,    naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl,    furanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,    pyrazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, benzofuran-2-yl or    1,2,3-triazol-4-yl,    -   optionally mono- to trisubstituted independently of one another        by    -   fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,        trifluoromethyl, methoxy, ethoxy, methyl-S(O)_(m)—,        ethyl-S(O)_(m)—, cyclopropylmethyl-S(O)_(m)—, difluoromethoxy,        trifluoromethoxy, trifluoromethyl-S(O)_(m)—,        difluoroethyl-S(O)_(m)—, trifluoroethyl-S(O)_(m)—,        (tetrahydro-2H-pyran-4-yloxy)methyl, dimethylsulphamoyl,        methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoethoxy,        (cyclopropylcarbonyl)oxy, morpholin-4-yl, dimethylamino,        diethylamino, ethylmethylamino, cyano and phenyl, naphthyl,        pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, furanyl,        thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,        pyrazolyl, imidazolyl, oxadiazolyl, thiadiazolyl,        benzofuran-2-yl or 1,2,3-triazol-4-yl, optionally mono- to        trisubstituted independently of one another by fluorine,        chlorine, bromine, methyl, ethyl, difluoromethyl,        trifluoromethyl, methoxy, ethoxy, methyl-S(O)_(m)—,        ethyl-S(O)_(m)—, cyclopropylmethyl-S(O)_(n)—, difluoromethoxy,        trifluoromethoxy, trifluoromethyl-S(O)_(m)—,        difluoroethyl-S(O)_(m)—, trifluoroethyl-S(O)_(m)—,        (tetrahydro2H-pyran-4-yloxy)methyl, dimethylsulphamoyl,        methoxycarbonyl, ethoxycarbonyl, 2-ethoxy2-oxoethoxy,        (cyclopropylcarbonyl)oxy, morpholin-4-yl or cyano,    -   or    -   represents a phenyl which has a chain consisting of one or two        oxygen atoms and one or two carbon atoms attached to two        adjacent ring positions, thus forming an optionally partially        unsaturated heterocyclic ring,

Very particularly preferred substituents or ranges of the radicals shownin the compounds of the formula (II) are illustrated below. Thecombination thereof forms the range of preference (5-1).

-   Q represents oxygen or sulphur and preferably oxygen,-   V represents hydrogen,-   W represents a radical from the group consisting of hydrogen,    chlorine and bromine and preferably represents hydrogen,-   X represents a radical from the group consisting of    3-[(2,2,2-trifluoroethyl)sulphanyl]phenyl,    2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl,    3-(methylsulphanyl)phenyl, pyrimidin-2-yl,    3-[(2,2,2-trifluoroethyl)sulphinyl]phenyl, phenyl, pyridin-3-yl,    3,5-dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl,    2,4-dichlorophenyl, 3,4-dichlorophenyl, 1-methyl-1H-pyrrol-2-yl,    3-furyl, 2,5-dimethyl-3-thienyl,    3-[(trifluoromethyl)sulphanyl]phenyl,    3-[(cyclopropylmethyl)sulphanyl]phenyl, 3-(methoxymethyl)phenyl,    3-[(tetrahydro-2H-pyran-4-yloxy)methyl]phenyl,    3-(dimethylsulphamoyl)phenyl, 3-(methylsulphonyl)phenyl,    4-methyl-3-(methylsulphanyl)phenyl,    1-(2-cyanophenyl)-1H-pyrazol-4-yl,    1-(4-fluorophenyl)-1H-pyrazol-4-yl, 1-phenyl-1H-pyrazol-4-yl,    1-naphthyl, 5-(methoxycarbonyl)-1-naphthyl,    4-fluoro-2-(methoxycarbonyl)phenyl, 4-fluoro-1-naphthyl,    4-chloro-3-(ethoxycarbonyl)phenyl, 2-(methoxycarbonyl)phenyl,    pyridin-4-yl, 6-(ethoxycarbonyl)pyridin-2-yl,    3-(ethoxycarbonyl)phenyl, 2-naphthyl,    4-methoxy-3-(methoxycarbonyl)phenyl,    4-chloro-2-(methoxycarbonyl)phenyl, 3-thienyl,    3-(2-ethoxy-2-oxoethoxy)-4-methylphenyl,    3-(2-ethoxy-2-oxoethoxy)phenyl,    3-(2-ethoxy-2-oxoethoxy)-4,5-difluorophenyl,    3-(2-ethoxy-2-oxoethoxy)-4-fluorophenyl,    3-(ethoxycarbonyl)-4-fluorophenyl,    (3-{[(cyclopropylcarbonyl)oxy]methyl}phenyl,    3-{[(cyclopropylcarbonyl)oxy]methyl}-4-fluorophenyl, pyridin-2-yl,    3-(difluoromethyl)phenyl, 3-[(trifluoromethyl)sulphinyl]phenyl,    4-fluoro-3-(trifluoromethyl)phenyl,    3-chloro-5-(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl,    3,5-bis(trifluoromethyl)phenyl, 3-fluoro-5-(trifluoromethyl)phenyl,    4-cyano-3-(trifluoromethyl)phenyl, 3-(2,2,2-trifluoroethyl)phenyl,    3-(pentafluoroethyl)phenyl, 3-cyanophenyl, 4-chloro-3-cyanophenyl,    3-cyano-5-fluorophenyl, 3-cyano-5-(trifluoromethyl)phenyl,    5-cyano-2-methoxyphenyl, 3-cyano-4-fluorophenyl,    5-cyanopyridin-3-yl, 5-cyano-6-(dimethylamino)pyridin-3-yl,    5-cyano-6-(morpholin-4-yl)pyridin-3-yl,    5-cyano-6-ethoxypyridin-3-yl, 5-cyano-6-methoxypyridin-3-yl,    3-chloro-5-cyanophenyl, 1-benzofuran-2-yl, 3-phenyl-1,2-oxazol-5-yl,    3-(ethoxycarbonyl)-1,2-oxazol-5-yl,    1-isopropyl-1H-1,2,3-triazol-4-yl, 1-methyl-1H-1,2,3-triazol-4-yl or    5-cyano-6-methoxypyridin-3-yl,-   Y represents methyl,-   A represents a radical from the group consisting of hydrogen, methyl    and ethyl and preferably represents methyl and ethyl and-   T represents an electron pair.

Furthermore very particularly preferred substituents or ranges of theradicals shown in the compounds of the formula (II) are illustratedbelow. The combination thereof forms the range of preference (5-2) forthe compounds of the formula (II) and their salts.

Here, the radicals Q, V, W, Y, A and T are as defined in range ofpreference (5-1) and

-   X represents a radical from the group consisting of    3-[(2,2,2-trifluoroethyl)sulphanyl]phenyl,    2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl,    3-(methylsulphanyl)phenyl, pyrimidin-2-yl,    3-[(2,2,2-trifluoroethyl)sulphinyl]phenyl, phenyl, pyridin-3-yl,    3,5-dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl,    2,4-dichlorophenyl, 3,4-dichlorophenyl, 1-methyl-1H-pyrrol-2-yl,    3-furyl, 2,5-dimethyl-3-thienyl,    3-[(trifluoromethyl)sulphanyl]phenyl,    3-[(cyclopropylmethyl)sulphanyl]phenyl, 3-(methoxymethyl)phenyl,    3-[(tetrahydro-2H-pyran-4-yloxy)methyl]phenyl,    3-(dimethylsulphamoyl)phenyl, 3-(methylsulphonyl)phenyl,    4-methyl-3-(methylsulphanyl)phenyl,    1-(2-cyanophenyl)-1H-pyrazol-4-yl,    1-(4-fluorophenyl)-1H-pyrazol-4-yl, 1-phenyl-1H-pyrazol-4-yl,    1-naphthyl, 5-(methoxycarbonyl)-1-naphthyl,    4-fluoro-2-(methoxycarbonyl)phenyl, 4-fluoro-1-naphthyl,    4-chloro-3-(ethoxycarbonyl)phenyl, 2-(methoxycarbonyl)phenyl,    pyridin-4-yl, 6-(ethoxycarbonyl)pyridin-2-yl,    3-(ethoxycarbonyl)phenyl, 2-naphthyl,    4-methoxy-3-(methoxycarbonyl)phenyl,    4-chloro-2-(methoxycarbonyl)phenyl, 3-thienyl,    3-(2-ethoxy-2-oxoethoxy)-4-methylphenyl,    3-(2-ethoxy-2-oxoethoxy)phenyl,    3-(2-ethoxy-2-oxoethoxy)-4,5-difluorophenyl,    3-(2-ethoxy-2-oxoethoxy)-4-fluorophenyl,    3-(ethoxycarbonyl)-4-fluorophenyl,    (3-{[(cyclopropylcarbonyl)oxy]methyl}phenyl,    3-{[(cyclopropylcarbonyl)oxy]methyl}-4-fluorophenyl, pyridin-2-yl,    3-(difluoromethyl)phenyl, 3-[(trifluoromethyl)sulphinyl]phenyl,    4-fluoro-3-(trifluoromethyl)phenyl,    3-chloro-5-(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl,    3,5-bis(trifluoromethyl)phenyl, 3-fluoro-5-(trifluoromethyl)phenyl,    4-cyano-3-(trifluoromethyl)phenyl, 3-(2,2,2-trifluoroethyl)phenyl,    3-(pentafluoroethyl)phenyl, 3-cyanophenyl, 4-chloro-3-cyanophenyl,    3-cyano-5-fluorophenyl, 3-cyano-5-(trifluoromethyl)phenyl,    5-cyano-2-methoxyphenyl, 3-cyano-4-fluorophenyl,    5-cyanopyridin-3-yl, 5-cyano-6-(dimethylamino)pyridin-3-yl,    5-cyano-6-(morpholin-4-yl)pyridin-3-yl,    5-cyano-6-ethoxypyridin-3-yl, 5-cyano-6-methoxypyridin-3-yl,    3-chloro-5-cyanophenyl, 1-benzofuran-2-yl, 3-phenyl-1,2-oxazol-5-yl,    3-(ethoxycarbonyl)-1,2-oxazol-5-yl,    1-isopropyl-1H-1,2,3-triazol-4-yl, 1-methyl-1H-1,2,3-triazol-4-yl,    5-cyano-6-methoxypyridin-3-yl, 6-methoxypyridin-2-yl,    2,3-dihydro-1-benzofuran-7-yl, 1-benzofuran-7-yl,    2,6-dimethoxypyridin-3-yl, 2-methoxyphenyl, 1,3-benzodioxol-4-yl,    2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl,    6-(trifluoromethyl)pyridin-2-yl, 5-chloro-2-methoxypyridin-3-yl,    2-methoxypyridin-3-yl, 6-ethoxypyridin-3-yl,    5-chloro-6-methoxypyridin-3-yl, 2-(methylsulphanyl)pyridin-3-yl,    2-ethoxypyridin-3-yl, 5,6-dimethoxypyridin-3-yl,    2-methoxypyridin-4-yl, 6-methoxy-5-(trifluoromethyl)pyridin-3-yl,    6-methoxy-5-nitropyridin-3-yl, 2,6-dimethoxypyridin-4-yl,    2-(methylsulphanyl)phenyl,    2-methoxy-6-(trifluoromethyl)pyridin-4-yl, 3-cyano-5-methoxyphenyl,    5-fluoro-2-methoxypyridin-3-yl, 6-isopropoxypyridin-3-yl,    6-methoxypyridin-3-yl, 2-(2-amino-2-oxoethoxy)phenyl,    3-cyano-4-isopropoxyphenyl and 3-chloropyridin-2-yl.

In range of preference (1-1) or (1-2), unless stated otherwise,

halogen is selected from the group of fluorine, chlorine, bromine andiodine, preferably in turn from the group of fluorine, chlorine andbromine,

hetaryl (synonymous with heteroaryl, including as part of a larger unit,for example hetarylalkyl) is selected from the group consisting offuryl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl,1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl,pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, benzofuryl, benzoisofuryl, benzothienyl,benzoisothienyl, indolyl, isoindolyl, indazolyl, benzothiazolyl,benzoisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl,2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, cinnolinyl,phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl,benzotriazinyl, purinyl, pteridinyl and indolizinyl,

heterocyclyl represents a saturated 3-, 4-, 5- or 6-membered ring whichcontains 1 or 2 nitrogen atoms and/or one oxygen atom and/or one sulphuratom, but where 2 nitrogen atoms shall not be directly vicinal, forexample aziridinyl, azetidinyl, azolidinyl, azinanyl, oxiranyl,oxetanyl, oxolanyl, oxanyl, dioxanyl, thiiranyl, thietanyl, thiolanyl,thianyl and tetrahydrofuryl.

In range of preference (2-1) or (2-2), unless stated otherwise,

halogen represents fluorine, chlorine, bromine and iodine, preferablyfluorine, chlorine and bromine,

hetaryl (including as part of a larger unit, such as hetarylalkyl)represents pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl,furanyl, benzyl, pyridinylmethyl and thiazolylmethyl, and

heterocyclyl (including as part of a larger unit, such asheterocyclylalkyl) represents a saturated or unsaturated 3-, 4- or5-membered ring which contains 1 or 2 nitrogen atoms and/or one oxygenatom and/or one sulphur atom, but where 2 nitrogen atoms shall not bedirectly vicinal, for example 1- or 2-aziridinyl, 2-oxiranyl,2-thiiranyl, 1- or 2-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl,1,3-dioxetan-2-yl, 1-, 2- or 3-pyrrolidinyl.

In range of preference (3-1) or (3-2), unless stated otherwise,

halogen represents fluorine, chlorine, bromine and iodine, preferablyfluorine, chlorine and bromine, and

heterocyclyl (including as part of a larger unit, such asheterocyclylalkyl) represents a saturated or unsaturated 3- or4-membered ring which contains 1 or 2 nitrogen atoms and/or one oxygenatom and/or one sulphur atom, but where 2 nitrogen atoms shall not bedirectly vicinal, for example 1- or 2-aziridinyl, 2-oxiranyl,2-thiiranyl, 1- or 2-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl or1,3-dioxetan-2-yl. Halogen-substituted radicals, for example haloalkyl,are, unless otherwise specified, monohalogenated or polyhalogenated upto the maximum number of possible substituents. In the case ofpolyhalogenation, the halogen atoms may be identical or different. Inthis case, halogen is fluorine, chlorine, bromine or iodine, especiallyfluorine, chlorine or bromine.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,may each be straight-chain or branched if possible, including incombination with heteroatoms, as, for example, in alkoxy.

Unless stated otherwise, optionally substituted radicals may be mono- orpolysubstituted, where the substituents in the case of polysubstitutionsmay be the same or different.

If, in the compounds of the formula (I), T represents oxygen, thesecompounds are present as N-oxides.

If, in the compounds of the formula (I), T represents an electron pair,these compounds are present as pyridines.

The radical definitions or elucidations given in general terms or listedwithin areas of preference apply correspondingly to end products and tostarting materials and intermediates. These radical definitions can becombined with one another as desired, i.e. including combinationsbetween the respective ranges of preference.

Preference according to the invention is given to using compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred (range of preference (1-1) or range of preference(1-2)).

Particular preference according to the invention is given to usingcompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred (range of preference (2-1)or range of preference (2-2)).

Very particular preference according to the invention is given to usingcompounds of the formula (II) which contain a combination of thedefinitions listed above as being very particularly preferred (range ofpreference (3-1) or (3-2)).

Even more preference according to the invention is given to usingcompounds of the formula (II) which contain a combination of thedefinitions listed above as being very particularly preferred (range ofpreference (4-1) or range of preference (4-2)).

Even more preference according to the invention is given to usingcompounds of the formula (II) which contain a combination of thedefinitions listed above as being very particularly preferred (range ofpreference (5-1) or range of preference (5-2)).

In a preferred embodiment, the invention relates to the compounds of theformula (I) or of the formula (II), where the radicals Q, V, W, Y, m, A,R² and T are as defined in range of preference (1-1) or range ofpreference (1-2) or range of preference (2-1) or range of preference(2-2) or range of preference (3-1) or range of preference (3-2) or rangeof preference (4-1) or range of preference (4-2) or range of preference(5-1) or range of preference (5-2) and

X has the meanings described in embodiment (0).

In a preferred embodiment, the invention relates to the compounds of theformula (I) or of the formula (II), where the radicals Q, V, W, Y, m, A,R² and T are as defined in embodiment (0) or range of preference (2-1)or range of preference (2-2) or range of preference (3-1) or range ofpreference (3-2) or range of preference (4-1) or range of preference(4-2) or range of preference (5-1) or range of preference (5-2) and

X and L¹ and L² have the meanings described in range of preference (1-1)or (1-2).

In a preferred embodiment, the invention relates to the compounds of theformula (I) or of the formula (II), where the radicals Q, V, W, Y, m, A,R² and T are as defined in embodiment (0) or range of preference (1-1)or range of preference (1-2) or range of preference (3-1) or range ofpreference (3-2) or range of preference (4-1) or range of preference(4-2) or range of preference (5-1) or range of preference (5-2) and

X and L¹ and L² have the meanings described in range of preference (2-1)or (2-2).

In a preferred embodiment, the invention relates to the compounds of theformula (I) or of the formula (II), where the radicals Q, V, W, Y, m, A,R² and T are as defined in embodiment (0) or range of preference (1-1)or range of preference (1-2) or range of preference (2-1) or range ofpreference (2-2) or range of preference (4-1) or range of preference(4-2) or range of preference (5-1) or range of preference (5-2) and

X has the meanings described in range of preference (3-1) or (3-2).

In a preferred embodiment, the invention relates to the compounds of theformula (I) or of the formula (II), where the radicals Q, V, W, Y, m, A,R² and T are as defined in embodiment (0) or range of preference (1-1)or range of preference (1-2) or range of preference (2-1) or range ofpreference (2-2) or range of preference (3-1) or range of preference(3-2) or range of preference (5-1) or range of preference (5-2) and

X has the meanings described in range of preference (4-1) or range ofpreference (4-2).

In a preferred embodiment, the invention relates to the compounds of theformula (I) or of the formula (II), where the radicals Q, V, W, Y, m, A,R² and T are as defined in embodiment (0) or range of preference (1-1)or range of preference (1-2) or range of preference (2-1) or range ofpreference (2-2) or range of preference (3-1) or range of preference(3-2) or range of preference (4-1) or range of preference (4-2) and

X has the meanings described in range of preference (5-1) or range ofpreference (5-2).

The invention furthermore provides intermediates of the formulae (Xa-Xd)

where the radicals present have the meanings according to theabove-mentioned embodiments according to the invention of the compoundof the formula (I) or (II) or preferably according to any of the rangesof preference (1-1), (1-2), (2-1), (2-2), (3-1), (3-2), (4-1), (4-2),(5-1) or (5-2) and particularly preferably according to range ofpreference (5-1) or (5-2).

Isomers

Depending on the nature of the substituents, the compounds of theformula (I) may be in the form of geometric and/or optically activeisomers or corresponding isomer mixtures in different compositions.

These stereoisomers are, for example, enantiomers, diastereomers,atropisomers or geometric isomers. The invention therefore encompassesboth pure stereoisomers and any desired mixtures of these isomers.

Methods and Uses

Hereinbelow, the statements concerning the compounds of the formula (I)do, of course, also apply to the compounds of the formula (II) which areembraced by formula (I).

The invention also relates to methods for controlling animal pests, inwhich compounds of the formula (I) are allowed to act on animal pestsand/or their habitat. The control of the animal pests is preferablyconducted in agriculture and forestry, and in material protection. Thispreferably excludes methods for surgical or therapeutic treatment of thehuman or animal body and diagnostic methods carried out on the human oranimal body.

The invention further relates to the use of the compounds of the formula(I) as pesticides, in particular crop protection agents.

In the context of the present application, the term “pesticide” in eachcase also always encompasses the term “crop protection agent”.

The compounds of the formula (I), given good plant tolerance, favourableendotherm toxicity and good environmental compatibility, are suitablefor protecting plants and plant organs against biotic and abiotic stressfactors, for increasing harvest yields, for improving the quality of theharvested material and for controlling animal pests, especially insects,arachnids, helminths, especially nematodes and molluscs, which areencountered in agriculture, in horticulture, in animal husbandry, inaquatic cultures, in forests, in gardens and leisure facilities, in theprotection of stored products and of materials, and in the hygienesector.

In the context of the present patent application, the term “hygiene”should be understood to mean any and all measures, provisions andprocedures which have the aim of preventing diseases, especiallyinfection diseases, and which serve to protect the health of humans andanimals and/or protect the environment and/or maintain cleanliness.According to the invention, this especially includes measures forcleaning, disinfection and sterilization, for example of textiles orhard surfaces, especially surfaces made of glass, wood, cement,porcelain, ceramic, plastic or else metal(s), in order to ensure thatthese are free of hygiene pests and/or their secretions. The scope ofprotection of the invention in this regard preferably excludes surgicalor therapeutic treatment procedures to be applied to the human body orthe bodies of animals, and diagnostic procedures which are conducted onthe human body or the bodies of animals.

The term “hygiene sector” covers all areas, technical fields andindustrial applications in which these hygiene measures, provisions andprocedures are important, for example with regard to hygiene inkitchens, bakeries, airports, bathrooms, swimming pools, departmentstores, hotels, hospitals, stables, animal keeping, etc.

The term “hygiene pest” should therefore be understood to mean one ormore animal pests whose presence in the hygiene sector is problematic,especially for reasons of health. A main aim is therefore that ofavoiding, or limiting to a minimum degree, the presence of hygiene pestsand/or the exposure to these in the hygiene sector. This can especiallybe achieved through the use of a pesticide which can be used both forprevention of infestation and for prevention of an existing infestation.It is also possible to use formulations which prevent or reduce exposureto pests. Hygiene pests include, for example, the organisms mentionedbelow.

The term “hygiene protection” thus covers all acts by which thesehygiene measures, provisions and procedures are maintained and/orimproved.

The compounds of the formula (I) can preferably be used as pesticides.They are active against normally sensitive and resistant species andalso against all or specific stages of development. The above-mentionedpests include:

pests from the phylum of the Arthropoda, in particular from the class ofthe Arachnida, for example Acarus spp., e.g. Acarus siro, Aceria kuko,Aceria sheldoni, Aculops spp., Aculus spp., e.g. Aculus fockeui, Aculusschlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp.,Boophilus spp., Brevipalpus spp., e.g. Brevipalpus phoenicis, Bryobiagraminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp.,Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoidesfarinae, Dermacentor spp., Eotetranychus spp., e.g. Eotetranychushicoriae, Epitrimerus pyri, Eutetranychus spp., e.g. Eutetranychusbanksi, Eriophyes spp., e.g. Eriophyes pyri, Glycyphagus domesticus,Halotydeus destructor, Hemitarsonemus spp., e.g. Hemitarsonemus latus(=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectusspp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp.,Oligonychus spp., e.g. Oligonychus coffeae, Oligonychus coniferarum,Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus,Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi,Ornithodorus spp., Ornithonyssus spp., Panonychus spp., e.g. Panonychuscitri (=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi),Phyllocoptruta oleivora, Platytetranychus multidigituli,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemusspp., Steneotarsonemus spinki, Tarsonemus spp., e.g. Tarsonemusconfusus, Tarsonemus pallidus, Tetranychus spp., e.g. Tetranychuscanadensis, Tetranychus cinnabarinus, Tetranychus turkestani,Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasateslycopersici;

from the class of the Chilopoda, for example Geophilus spp., Scutigeraspp.;

from the order or the class of the Collembola, for example Onychiurusarmatus; Sminthurus viridis;

from the class of the Diplopoda, for example Blaniulus guttulatus;

from the class of the Insecta, for example from the order of theBlattodea e.g. Blatta orientalis, Blattella asahinai, Blattellagermanica, Leucophaea maderae, Loboptera decipiens, Neostylopygarhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., e.g.Periplaneta americana, Periplaneta australasiae, Pycnoscelussurinamensis, Supella longipalpa;

from the order of the Coleoptera, for example Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelasticaalni, Agriotes spp., e.g. Agriotes linneatus, Agriotes mancus,Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum,Anoplophora spp., Anthonomus spp., e.g. Anthonomus grandis, Anthrenusspp., Apion spp., Apogonia spp., Atomaria spp., e.g. Atomaria linearis,Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp.,e.g. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotomatrifurcata, Ceutorrhynchus spp., e.g. Ceutorrhynchus assimilis,Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., e.g.Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa,Cleonus mendicus, Conoderus spp., Cosmopolites spp., e.g. Cosmopolitessordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., e.g.Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi,Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi,Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturusadspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp.,e.g. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctatahowardi, Diabrotica undecimpunctata undecimpunctata, Diabroticavirgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp.,Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp.,e.g. Epilachna borealis, Epilachna varivestis, Epitrix spp., e.g.Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrixsubcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides,Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyxspp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomecessquamosus, Hypothenemus spp., e.g. Hypothenemus hampei, Hypothenemusobscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasiodermaserricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsadecemlineata, Leucoptera spp., e.g. Leucoptera coffeella, Lissorhoptrusoryzophilus, Listronotus (=Hyperodes) spp., Lixus spp., Luperodes spp.,Luperomorpha xanthodera, Lyctus spp., Megascelis spp., Melanotus spp.,e.g. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp.,e.g. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactusxanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus,Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae,Otiorhynchus spp., e.g. Otiorhynchus cribricollis, Otiorhynchusligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus,Otiorhynchus sulcatus, Oulema spp., e.g. Oulema melanopus, Oulemaoryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Phyllophaga helleri, Phyllotreta spp., e.g. Phyllotreta armoraciae,Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popilliajaponica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp.,e.g. Psylliodes affinis, Psylliodes chrysocephala, Psylliodespunctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica,Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum,Sinoxylon perforans, Sitophilus spp., e.g. Sitophilus granarius,Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorusspp., Stegobium paniceum, Sternechus spp., e.g. Sternechus paludatus,Symphyletes spp., Tanymecus spp., e.g. Tanymecus dilaticollis, Tanymecusindicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioidesmauretanicus, Tribolium spp., e.g. Tribohum audax, Tribolium castaneum,Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp.,Zabrus spp., e.g. Zabrus tenebrioides;

from the order of the Dermaptera, for example Anisolabis maritime,Forficula auricularia, Labidura riparia;

from the order of the Diptera, for example Aedes spp., e.g. Aedesaegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp.,e.g. Agromyza frontella, Agromyza parvicornis, Anastrepha spp.,Anopheles spp., e.g. Anopheles quadrimaculatus, Anopheles gambiae,Asphondylia spp., Bactrocera spp., e.g. Bactrocera cucurbitae,Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphoraerythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp.,Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp.,Contarinia spp., e.g. Contarinia johnsoni, Contarinia nasturtii,Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola,Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris,Culex spp., e.g. Culex pipiens, Culex quinquefasciatus, Culicoides spp.,Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., e.g.Dasineura brassicae, Delia spp., e.g. Delia antiqua, Delia coarctata,Delia florilega, Delia platura, Delia radicum, Dermatobia hominis,Drosophila spp., e.g. Drosphila melanogaster, Drosophila suzukii,Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp.,Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola,Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., e.g.Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Luciliaspp., e.g. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp.,e.g. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinellafrit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya orPegomyia spp., e.g. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora,Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platypareapoeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., e.g.Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletisindifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp.,Simulium spp., e.g. Simulium meridionale, Stomoxys spp., Tabanus spp.,Tetanops spp., Tipula spp., e.g. Tipula paludosa, Tipula simplex,Toxotrypana curvicauda;

from the order of the Hemiptera, for example Acizzia acaciaebaileyanae,Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiponspp., e.g. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp.,Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobusbarodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrascaspp., e.g. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui,Aonidiella spp., e.g. Aonidiella aurantii, Aonidiella citrina,Aonidiella inornata, Aphanostigma pini, Aphis spp., e.g. Aphiscitricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines,Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni,Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphisviburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp.,Aspidiotus spp., e.g. Aspidiotus nerii, Atanus spp., Aulacorthum solani,Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae,Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae,Cacopsylla spp., e.g. Cacopsylla pyricola, Calligypona marginata,Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera,Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspistegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola,Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila,Coccomytilus halli, Coccus spp., e.g. Coccus hesperidum, Coccuslongulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis,Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodeschittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp.,Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., e.g.Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccusspp., Empoasca spp., e.g. Empoasca abrupta, Empoasca fabae, Empoascamaligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., e.g.Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneuraspp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisiaspp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspisspp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodiscacoagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., e.g.Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphaxstriatellus, Lecanium spp., e.g. Lecanium corni (=Parthenolecaniumcorni), Lepidosaphes spp., e.g. Lepidosaphes ulmi, Lipaphis erysimi,Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., e.g.Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae,Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiellaspp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis,Monelliopsis pecanis, Myzus spp., e.g. Myzus ascalonicus, Myzus cerasi,Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae,Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., e.g.Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra,Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxyachinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., e.g.Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., e.g. Pemphigusbursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp.,Phenacoccus spp., e.g. Phenacoccus madeirensis, Phloeomyzus passerinii,Phorodon humuli, Phylloxera spp., e.g. Phylloxera devastatrix,Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., e.g.Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis,Pseudaulacaspis pentagona, Pseudococcus spp., e.g. Pseudococcuscalceolariae, Pseudococcus comstocki, Pseudococcus longispinus,Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psyllaspp., e.g. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp.,Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., e.g.Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis,Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp.,Rhopalosiphum spp., e.g. Rhopalosiphum maidis, Rhopalosiphumoxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetiaspp., e.g. Saissetia coffeae, Saissetia miranda, Saissetia neglecta,Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidusarticulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatellafurcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae,Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae,Tomaspis spp., Toxoptera spp., e.g. Toxoptera aurantii, Toxopteracitricidus, Trialeurodes vaporariorum, Trioza spp., e.g. Triozadiospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;

from the suborder of the Heteroptera, for example Aelia spp., Anasatristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp.,Campylomma livida, Cavelerius spp., Cimex spp., e.g. Cimex adjunctus,Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp.,Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocorishewetti, Dysdercus spp., Euschistus spp., e.g. Euschistus heros,Euschistus servus, Euschistus tristigmus, Euschistus variolarius,Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp.,Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis,Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., e.g.Lygocoris pabulinus, Lygus spp., e.g. Lygus elisus, Lygus hesperus,Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae,Monalonion atratum, Nezara spp., e.g. Nezara viridula, Nysius spp.,Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., e.g.Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp.,Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp.,Stephanitis nashi, Tibraca spp., Triatoma spp.;

from the order of the Hymenoptera, for example Acromyrmex spp., Athaliaspp., e.g. Athalia rosae, Atta spp., Camponotus spp., Dolichovespulaspp., Diprion spp., e.g. Diprion similis, Hoplocampa spp., e.g.Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema(Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp.,Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta,Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., e.g.Vespa crabro, Wasmannia auropunctata, Xeris spp.;

from the order of the Isopoda, for example Armadillidium vulgare,Oniscus asellus, Porcellio scaber;

from the order of the Isoptera, for example Coptotermes spp., e.g.Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp.,Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermesspp., Odontotermes spp., Porotermes spp., Reticulitermes spp., e.g.Reticulitermes flavipes, Reticulitermes hesperus;

from the order of the Lepidoptera, for example Achroia grisella,Acronicta major, Adoxophyes spp., e.g. Adoxophyes orana, Aedialeucomelas, Agrotis spp., e.g. Agrotis segetum, Agrotis ipsilon, Alabamaspp., e.g. Alabama argillacea, Amyelois transitella, Anarsia spp.,Anticarsia spp., e.g. Anticarsia gemmatalis, Argyroploce spp.,Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara,Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoeciaspp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella,Carposina niponensis, Cheimatobia brumata, Chilo spp., e.g. Chiloplejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp.,Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp.,Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp.,Conotrachelus spp., Copitarsia spp., Cydia spp., e.g. Cydia nigricana,Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp.,Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpuslignosellus, Eldana saccharina, Ephestia spp., e.g. Ephestia elutella,Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp.,Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp.,Eupoecilia ambiguella, Euproctis spp., e.g. Euproctis chrysorrhoea,Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp.,Grapholitha spp., e.g. Grapholita molesta, Grapholita prunivora,Hedylepta spp., Helicoverpa spp., e.g. Helicoverpa armigera, Helicoverpazea, Heliothis spp., e.g. Heliothis virescens Hofmannophilapseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella,Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresiamolesta, Leucinodes orbonalis, Leucoptera spp., e.g. Leucopteracoffeella, Lithocolletis spp., e.g. Lithocolletis blancardella,Lithophane antennata, Lobesia spp., e.g. Lobesia botrana, Loxagrotisalbicosta, Lymantria spp., e.g. Lymantria dispar, Lyonetia spp., e.g.Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestrabrassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimnaseparata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisaspp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., e.g.Ostrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp.,e.g. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp.,e.g. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycterspp., e.g. Phyllonorycter blancardella, Phyllonorycter crataegella,Pieris spp., e.g. Pieris rapae, Platynota stultana, Plodiainterpunctella, Plusia spp., Plutella xylostella (=Plutellamaculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletiaspp., e.g. Pseudaletia unipuncta, Pseudoplusia includens, Pyraustanubilalis, Rachiplusia nu, Schoenobius spp., e.g. Schoenobiusbipunctifer, Scirpophaga spp., e.g. Scirpophaga innotata, Scotiasegetum, Sesamia spp., e.g. Sesamia inferens, Sparganothis spp.,Spodoptera spp., e.g. Spodoptera eradiana, Spodoptera exigua, Spodopterafrugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp.,Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora,Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tineapellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella,Trichoplusia spp., e.g. Trichoplusia ni, Tryporyza incertulas, Tutaabsoluta, Virachola spp.;

from the order of the Orthoptera or Saltatoria, for example Achetadomesticus, Dichroplus spp., Gryllotalpa spp., e.g. Gryllotalpagryllotalpa, Hieroglyphus spp., Locusta spp., e.g. Locusta migratoria,Melanoplus spp., e.g. Melanoplus devastator, Paratlanticus ussuriensis,Schistocerca gregaria;

from the order of the Phthiraptera, for example Damalinia spp.,Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxeravastatrix, Phthirus pubis, Trichodectes spp.;

from the order of the Psocoptera, for example Lepinotus spp., Liposcelisspp.;

from the order of the Siphonaptera, for example Ceratophyllus spp.,Ctenocephalides spp., e.g. Ctenocephalides canis, Ctenocephalides felis,Pulex irritans, Tunga penetrans, Xenopsylla cheopis;

from the order of the Thysanoptera, for example Anaphothrips obscurus,Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri,Enneothrips flavens, Frankliniella spp., e.g. Frankliniella fusca,Frankliniella occidentalis, Frankliniella schultzei, Frankliniellatritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothripsspp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp.,Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi,Thrips spp., e.g. Thrips palmi, Thrips tabaci;

from the order of the Zygentoma (=Thysanura), for example Ctenolepismaspp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;

from the class of the Symphyla, for example Scutigerella spp., e.g.Scutigerella immaculata;

pests from the phylum of the Mollusca, for example from the class of theBivalvia, e.g. Dreissena spp.;

and also from the class of the Gastropoda, for example Anion spp., e.g.Anion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., e.g.Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomaceaspp., Succinea spp.;

plant pests from the phylum of the Nematoda, i.e. plant-parasiticnematodes, in particular Aglenchus spp., e.g. Aglenchus agricola,Anguina spp., e.g. Anguina tritici, Aphelenchoides spp., e.g.Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp.,e.g. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimusnortoni, Bursaphelenchus spp., e.g. Bursaphelenchus cocophilus,Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp.,e.g. Cacopaurus pestis, Criconemella spp., e.g. Criconemella curvata,Criconemella onoensis, Criconemella ornata, Criconemella rusium,Criconemella xenoplax (=Mesocriconema xenoplax), Criconemoides spp.,e.g. Criconemoides ferniae, Criconemoides onoense, Criconemoidesornatum, Ditylenchus spp., e.g. Ditylenchus dipsaci, Dolichodorus spp.,Globodera spp., e.g. Globodera pallida, Globodera rostochiensis,Helicotylenchus spp., e.g. Helicotylenchus dihystera, Hemicriconemoidesspp., Hemicycliophora spp., Heterodera spp., e.g. Heterodera avenae,Heterodera glycines, Heterodera schachtii, Hirschmaniella spp.,Hoplolaimus spp., Longidorus spp., e.g. Longidorus africanus,Meloidogyne spp., e.g. Meloidogyne chitwoodi, Meloidogyne fallax,Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp.,Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp.,Paratrichodorus spp., e.g. Paratrichodorus minor, Paratylenchus spp.,Pratylenchus spp., e.g. Pratylenchus penetrans, Pseudohalenchus spp.,Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp.,e.g. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp.,Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp.,e.g. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp.,e.g. Tylenchorhynchus annulatus, Tylenchulus spp., e.g. Tylenchulussemipenetrans, Xiphinema spp., e.g. Xiphinema index.

The compounds of the formula (I) can optionally, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, asmicrobicides or gametocides, for example as fungicides, antimycotics,bactericides, virucides (including agents against viroids) or as agentsagainst MLO (mycoplasma-like organisms) and RLO (rickettsia-likeorganisms). They can, as the case may be, also be used as intermediatesor precursors for the synthesis of other active ingredients.

Formulations

The present invention further relates to formulations and use formsprepared therefrom as pesticides, for example drench, drip and sprayliquors, comprising at least one compound of the formula (I).Optionally, the use forms comprise further pesticides and/or adjuvantswhich improve action, such as penetrants, e.g. vegetable oils, forexample rapeseed oil, sunflower oil, mineral oils, for example paraffinoils, alkyl esters of vegetable fatty acids, for example rapeseed oilmethyl ester or soya oil methyl ester, or alkanol alkoxylates and/orspreaders, for example alkylsiloxanes and/or salts, for example organicor inorganic ammonium or phosphonium salts, for example ammoniumsulphate or diammonium hydrogenphosphate and/or retention promoters, forexample dioctyl sulphosuccinate or hydroxypropylguar polymers and/orhumectants, for example glycerol and/or fertilizers, for exampleammonium-, potassium- or phosphorus-containing fertilizers.

Customary formulations are, for example, water-soluble liquids (SL),emulsion concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and further possibleformulation types are de scribed, for example, by Crop LifeInternational and in Pesticide Specifications, Manual on development anduse of FAO and WHO specifications for pesticides, FAO Plant Productionand Protection Papers—173, prepared by the FAO/WHO Joint Meeting onPesticide Specifications, 2004, ISBN: 9251048576. The formulations, inaddition to one or more compounds of the formula (I), optionallycomprise further agrochemically active compounds.

Preference is given to formulations or use forms comprising auxiliaries,for example extenders, solvents, spontaneity promoters, carriers,emulsifiers, dispersants, frost protection agents, biocides, thickenersand/or further auxiliaries, for example adjuvants. An adjuvant in thiscontext is a component which enhances the biological effect of theformulation, without the component itself having any biological effect.Examples of adjuvants are agents which promote retention, spreading,attachment to the leaf surface or penetration.

These formulations are produced in a known manner, for example by mixingthe compounds of the formula (I) with auxiliaries, for exampleextenders, solvents and/or solid carriers and/or other auxiliaries, forexample surfactants. The formulations are produced either in suitablefacilities or else before or during application.

The auxiliaries used may be substances suitable for imparting specialproperties, such as certain physical, technical and/or biologicalproperties, to the formulation of the compounds of the formula (I), orto the use forms prepared from these formulations (for exampleready-to-use pesticides such as spray liquors or seed-dressingproducts).

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the simple and substituted amines, amides,lactams (such as N-alkylpyrrolidones) and lactones, the sulphones andsulphoxides (such as dimethyl sulphoxide).

If the extender utilized is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Useful liquid solventsare essentially: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example mineral oilfractions, mineral and vegetable oils, alcohols such as butanol orglycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulphoxide, and alsowater.

In principle, it is possible to use all suitable solvents. Examples ofsuitable solvents are aromatic hydrocarbons, for example xylene, tolueneor alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatichydrocarbons, for example chlorobenzene, chloroethylene or methylenechloride, aliphatic hydrocarbons, for example cyclohexane, paraffins,petroleum fractions, mineral and vegetable oils, alcohols, for examplemethanol, ethanol, isopropanol, butanol or glycol and their ethers andesters, ketones, for example acetone, methyl ethyl ketone, methylisobutyl ketone or cyclohexanone, strongly polar solvents, for exampledimethyl sulphoxide, and water.

In principle, it is possible to use all suitable carriers. Usefulcarriers especially include, for example, ammonium salts and natural,finely ground rocks, such as kaolins, aluminas, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and synthetic,finely ground rocks, such as highly disperse silica, aluminium oxide andnatural or synthetic silicates, resins, waxes and/or solid fertilizers.It is likewise possible to use mixtures of such carriers. Usefulcarriers for granules include: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite, dolomite, andsynthetic granules of inorganic and organic flours, and also granules oforganic material such as sawdust, paper, coconut shells, maize cobs andtobacco stalks.

It is also possible to use liquefied gaseous extenders or solvents.Especially suitable extenders or carriers are those which are gaseous atstandard temperature and under atmospheric pressure, for example aerosolpropellants such as halogenated hydrocarbons, and also butane, propane,nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam formers, dispersants or wettingagents having ionic or nonionic properties or mixtures of thesesurface-active substances are salts of polyacrylic acid, salts oflignosulphonic acid, salts of phenolsulphonic acid ornaphthalenesulphonic acid, polycondensates of ethylene oxide with fattyalcohols or with fatty acids or with fatty amines, with substitutedphenols (preferably alkylphenols or arylphenols), salts ofsulphosuccinic esters, taurine derivatives (preferably alkyl taurates),phosphoric esters of polyethoxylated alcohols or phenols, fatty acidesters of polyols, and derivatives of the compounds containingsulphates, sulphonates and phosphates, for example alkylaryl polyglycolethers, alkylsulphonates, alkyl sulphates, arylsulphonates, proteinhydrolysates, lignosulphite waste liquors and methylcellulose. Thepresence of a surfactant is advantageous if one of the compounds of theformula (I) and/or one of the inert carriers is insoluble in water andwhen the application takes place in water.

Further auxiliaries which may be present in the formulations and the useforms derived therefrom include dyes such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organic dyessuch as alizarin dyes, azo dyes and metal phthalocyanine dyes, andnutrients and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

Additional components which may be present are stabilizers, such as coldstabilizers, preservatives, antioxidants, light stabilizers, or otheragents which improve chemical and/or physical stability. Foam generatorsor antifoams may also be present.

In addition, the formulations and the use forms derived therefrom mayalso comprise, as additional auxiliaries, stickers such ascarboxymethylcellulose and natural and synthetic polymers in the form ofpowders, granules or latices, such as gum arabic, polyvinyl alcohol andpolyvinyl acetate, or else natural phospholipids such as cephalins andlecithins and synthetic phospholipids. Further auxiliaries may bemineral and vegetable oils.

It is possible if appropriate for still further auxiliaries to bepresent in the formulations and the use forms derived therefrom.Examples of such additives are fragrances, protective colloids, binders,adhesives, thickeners, thixotropic agents, penetrants, retentionpromoters, stabilizers, sequestrants, complexing agents, humectants,spreaders. In general, the compounds of the formula (I) can be combinedwith any solid or liquid additive commonly used for formulationpurposes.

Useful retention promoters include all those substances which reducedynamic surface tension, for example dioctyl sulphosuccinate, orincrease viscoelasticity, for example hydroxypropylguar polymers.

Useful penetrants in the present context are all those substances whichare typically used to improve the penetration of active agrochemicalingredients into plants. Penetrants are defined in this context by theirability to penetrate from the (generally aqueous) application liquorand/or from the spray coating into the cuticle of the plant and hence toincrease the mobility of the active ingredients in the cuticle. Themethod described in the literature (Baur et al., 1997, Pesticide Science51, 131-152) can be used for determining this property. Examples includealcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecylethoxylate (12), fatty acid esters, for example rapeseed oil methylester or soya oil methyl ester, fatty amine alkoxylates, for exampletallowamine ethoxylate (15), or ammonium and/or phosphonium salts, forexample ammonium sulphate or diammonium hydrogenphosphate.

The formulations preferably comprise between 0.00000001% and 98% byweight of the compound of the formula (I), more preferably between 0.01%and 95% by weight of the compound of the formula (I), most preferablybetween 0.5% and 90% by weight of the compound of the formula (I), basedon the weight of the formulation.

The content of the compound of the formula (I) in the use forms preparedfrom the formulations (in particular pesticides) may vary within wideranges. The concentration of the compound of the formula (I) in the useforms may typically be between 0.00000001% and 95% by weight of thecompound of the formula (I), preferably between 0.00001% and 1% byweight, based on the weight of the use form. Application is accomplishedin a customary manner appropriate for the use forms.

Mixtures

The compounds of the formula (I) can also be used in a mixture with oneor more suitable fungicides, bactericides, acaricides, molluscicides,nematicides, insecticides, microbiological agents, beneficial organisms,herbicides, fertilizers, bird repellents, phytotonics, sterilants,safeners, semiochemicals and/or plant growth regulators, in order thus,for example, to broaden the spectrum of action, prolong the period ofaction, enhance the rate of action, prevent repellency or preventevolution of resistance. In addition, active ingredient combinations ofthis kind can improve plant growth and/or tolerance to abiotic factors,for example high or low temperatures, to drought or to elevated watercontent or soil salinity. It is also possible to improve flowering andfruiting performance, optimize germination capacity and rootdevelopment, facilitate harvesting and improve yields, influencematuration, improve the quality and/or the nutritional value of theharvested products, prolong storage life and/or improve theprocessability of the harvested products.

In addition, the compounds of the formula (I) may be present in amixture with other active compounds or semiochemicals such asattractants and/or bird repellents and/or plant activators and/or growthregulators and/or fertilizers. Likewise, the compounds of the formula(I) can be used to improve plant properties, for example growth, yieldand quality of the harvested material.

In a particular embodiment according to the invention, the compounds ofthe formula (I) are present in formulations or in the use forms preparedfrom these formulations in a mixture with further compounds, preferablythose as described below.

If one of the compounds mentioned below can occur in differenttautomeric forms, these forms are also included even if not explicitlymentioned in each case. All the mixing components mentioned, as the casemay be, may also form salts with suitable bases or acids if they arecapable of doing so on the basis of their functional groups.

Insecticides/Acaricides/Nematicides

The active compounds specified here with their common names are knownand are described for example in “The Pesticide Manual”, 16th ed.,British Crop Protection Council 2012, or can be searched for on theInternet (e.g. http://www.alanwood.net/pesticides). The classificationis based on the IRAC Mode of Action Classification Scheme applicable atthe time of filing of this patent application.

(1) Acetylcholinesterase (AChE) inhibitors, for example carbamates, e.g.alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim,butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb,fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl,metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox,triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, e.g.acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos,chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl,coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate,heptenophos, imicyafos, isofenphos, isopropylO-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate,phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos,propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos,sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos,thiometon, triazophos, triclorfon and vamidothion.

(2) GABA-gated chloride channel blockers, for examplecyclodiene-organochlorines, e.g. chlordane and endosulfan orphenylpyrazoles (fiproles), e.g. ethiprole and fipronil.

(3) Sodium channel modulators, for example pyrethroids, e.g.acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin,bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer,bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin,beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin[(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R) isomer],esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate,flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin,momfluorothrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin,pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin,tetramethrin, tetramethrin [(1R) isomer], tralomethrin and transfluthrinor DDT or methoxychlor.

(4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, forexample neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine orsulfoxaflor or flupyradifurone.

(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, forexample spinosyns, e.g. spinetoram and spinosad.

(6) Glutamate-gated chloride channel (GluCl) allosteric modulators, forexample avermectins/milbemycins, e.g. abamectin, emamectin benzoate,lepimectin and milbemectin.

(7) Juvenile hormone mimetics, for example juvenile hormone analogues,e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

(8) Miscellaneous non-specific (multisite) inhibitors, for example alkylhalides, e.g. methyl bromide and other alkyl halides; or chloropicrin orsulphuryl fluoride or borax or tartar emetic or methyl isocyanategenerator, e.g. diazomet and metam.

(9) Chordotonal organ modulators, e.g. pymetrozine or flonicamide.

(10) Mite growth inhibitors, for example clofentezine, hexythiazox anddiflovidazin or etoxazole.

(11) Microbial disruptors of the insect midgut membrane, for exampleBacillus thuringiensis subspecies israelensis, Bacillus sphaericus,Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensissubspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis andB.t. plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, CrylA.105, Cry2Ab, VIP3A,mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/35Ab1.

(12) Inhibitors of mitochondrial ATP synthase, such as ATP disruptors,for example diafenthiuron or organotin compounds, e.g. azocyclotin,cyhexatin and fenbutatin oxide or propargite or tetradifon.

(13) Uncouplers of oxidative phosphorylation via disruption of theproton gradient, for example chlorfenapyr, DNOC and sulfluramid.

(14) Nicotinic acetylcholine receptor channel blockers, for examplebensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.

(15) Inhibitors of chitin biosynthesis, type 0, for examplebistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,teflubenzuron and triflumuron.

(16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.

(17) Moulting disruptors (especially in the case of Diptera), forexample cyromazine.

(18) Ecdysone receptor agonists, for example chromafenozide,halofenozide, methoxyfenozide and tebufenozide.

(19) Octopamine receptor agonists, for example amitraz.

(20) Mitochondrial complex III electron transport inhibitors, forexample hydramethylnon or acequinocyl or fluacrypyrim.

(21) Mitochondrial complex I electron transport inhibitors, for exampleMETI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben,tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-dependent sodium channel blockers, for example indoxacarbor metaflumizone.

(23) Inhibitors of acetyl CoA carboxylase, for example tetronic andtetramic acid derivatives, e.g. spirodiclofen, spiromesifen andspirotetramat.

(24) Mitochondrial complex IV electron transport inhibitors, for examplephosphines, e g aluminium phosphide, calcium phosphide, phosphine andzinc phosphide, or cyanides, calcium cyanide, potassium cyanide andsodium cyanide.

(25) Mitochondrial complex II electron transport inhibitors, for examplebeta-keto nitrile derivatives, e.g. cyenopyrafen and cyflumetofen andcarboxanilides, for example pyflubumide.

(28) Ryanodine receptor modulators, for example diamides, e.g.chlorantraniliprole, cyantraniliprole and flubendiamide,

further active ingredients, for example afidopyropen, afoxolaner,azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide,bromopropylate, chinomethionat, chloroprallethrin, cryolite,cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol,epsilon metofluthrin, epsilon momfluthrin, flometoquin,fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin,flufiprole, fluhexafon, fluopyram, fluralaner, fluxametamide,fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, kappabifenthrin, kappa tefluthrin, lotilaner, meperfluthrin, paichongding,pyridalyl, pyrifluquinazon, pyriminostrobin, spirobudiclofen,tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole,tioxazafen, thiofluoximate, triflumezopyrim and iodomethane;additionally preparations based on Bacillus firmus (1-1582, BioNeem,Votivo), and the following compounds:1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO2006/043635) (CAS 885026-50-6),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4′-piperidine]-1(2H)-yl}(2-chloropyridin-4-yl)methanone(known from WO2003/106457) (CAS 637360-23-7),2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide(known from WO2006/003494) (CAS 872999-66-1),3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO 2010052161) (CAS 1225292-17-0),3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethylcarbonate (known from EP 2647626) (CAS-1440516-42-6),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO2004/099160) (CAS 792914-58-0), PF1364 (known fromJP2010/018586) (CAS Reg.No. 1204776-60-2),N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(known from WO2012/029672) (CAS 1363400-41-2),(3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoropropan-2-one(known from WO2013/144213) (CAS 1461743-15-6),N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide(known from WO2010/051926) (CAS 1226889-14-0),5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide(known from CN103232431) (CAS 1449220-44-3),4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide,4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxido-3-thietanyl)benzamideand4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide(known from WO 2013/050317 A1) (CAS 1332628-83-7),N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulphinyl]propanamide,(+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulphinyl]propanamideand(−)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulphinyl]propanamide(known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1)(CAS 1477923-37-7),5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulphinyl]-1H-pyrazole-3-carbonitrile(known from CN 101337937 A) (CAS 1105672-77-2),3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide,(Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9);N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide(known from WO 2012/034403 A1) (CAS 1268277-22-0),N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide(known from WO 2011/085575 A1) (CAS 1233882-22-8),4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine(known from CN 101337940 A) (CAS 1108184-52-6); (2E)- and2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide(known from CN 101715774 A) (CAS 1232543-85-9); cyclopropanecarboxylicacid 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenylester (known from CN 103524422 A) (CAS 1542271-46-4);(4a5)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylicacid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2);6-deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-mannopyranose(known from US 2014/0275503 A1) (CAS 1181213-14-8);8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(CAS 1253850-56-4),(8-anti)-8-(2-cyclopropylmethoxy-4-trifluoro-methylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(CAS 933798-27-7),(8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8) andN-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propanamide(known from WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9).

Fungicides

The active compounds specified herein by their common name are known anddescribed, for example, in “Pesticide Manual” (16th Ed. British CropProtection Council) or searchable on the internet (for example:http://www.alanwood.net/pesticides).

All the mixing components mentioned in classes (1) to (15), as the casemay be, may form salts with suitable bases or acids if they are capableof doing so on the basis of their functional groups. All the fungicidalmixing components mentioned of classes (1) to (15), as the case may be,may include tautomeric forms.

1) Ergosterol biosynthesis inhibitors, for example (1.001)cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004)fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007)fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010)imazalil, (1.011) imazalil sulphate, (1.012) ipconazole, (1.013)metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016)prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019)pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022)tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025)triticonazole, (1.026)(1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.027)(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.028)(2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclo-propyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol(1.029)(2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.031)(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.032) (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.033)(25)-2-[4-(4-chloro-phenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.034)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.035)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.036)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.037)1-({(2R,45)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.038)1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.039)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.040)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluoro-phenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.041)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.042)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.043)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.044)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.045)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.046)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.047)2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.048)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.049)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.050)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.051)2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.052)2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.053)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.054)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol,(1.055)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.056)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.057)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.058)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.059)5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.060)5-(allylsulphanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.061)5-(allylsulphanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.062)5-(allylsulphanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.063)N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.064)N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.065)N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.066)N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.067)N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.068)N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.069)N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetra-fluoropropyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.070)N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.071)N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,(1.072)N′-(4-{[3-(difluoromethoxy)phenyl]sulphanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.073)N′-(4-{3-[(difluoromethyl)sulphanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.074)N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide,(1.075)N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide,(1.076)N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.077)N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.078)N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.079)N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.080)N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide.

2) Inhibitors of the respiratory chain in complex I or II, for example(2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004)carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad,(2.008) furametpyr, (2.009) isofetamid, (2.010) isopyrazam(anti-epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimericenantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate1RS,4SR,9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate1RS,4SR,9RS and the anti-epimeric racemate 1RS,4SR,9SR), (2.014)isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.015) isopyrazam(syn-epimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimericracemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019)pydiflumetofen, (2.020) pyraziflumid, (2.021) sedaxane, (2.022)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.023)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.024)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.025)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.026)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(2.027)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.028)3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.029)3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.030)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide,(2.031)3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.032)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.033)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine,(2.034)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.035)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.036)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.037)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.038)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.039)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.040)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.041)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.042)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.043)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.044)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.045)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,(2.046)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.047)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.048)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide,(2.049)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.050)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.051)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.052)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.053)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.054)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.055)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.056)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.

3) Inhibitors of the respiratory chain in complex III, for example(3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004)coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007)dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadon, (3.010)fenamidon, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013)kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016)picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019)pyraoxystrobin, (3.020) trifloxystrobin (3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide,(3.022)(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent3-enamide,(3.023)(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.024)(2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.025)(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate, (3.026)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.027)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide,(3.028)(2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide.

4) Mitosis and cell division inhibitors, for example (4.001)carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004)fluopicolid, (4.005) pencycuron, (4.006) thiabendazole, (4.007)thiophanate-methyl, (4.008) zoxamide, (4.009)3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(4.011)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine,(4.012)4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.013)4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.014)4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.015)4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.016)4-(2-bromo-4-fluorophenyl)-N-(2-chloro-phenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.017)4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.018)4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.019)4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.020)4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.021)4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.022)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(4.023)N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.024)N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.025)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine

5) Compounds having capacity for multisite activity, for example (5.001)Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004)chlorthalonil, (5.005) copper hydroxide (5.006) copper naphthenate,(5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(2+)sulphate, (5.010) dithianon, (5.011) dodin, (5.012) folpet, (5.013)mancozeb, (5.014) maneb, (5.015) metiram, (5.016) zinc metiram, (5.017)copper oxine, (5.018) propineb, (5.019) sulphur and sulphur preparationsincluding calcium polysulphide, (5.020) thiram, (5.021) zineb, (5.022)ziram.

6) Compounds capable of triggering host defence, for example (6.001)acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004)tiadinil.

7) Amino acid and/or protein biosynthesis inhibitors, for example(7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycinhydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil,(7.006)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

(8) ATP production inhibitors, for example (8.001) silthiofam.

9) Cell wall synthesis inhibitors, for example (9.001) benthiavalicarb,(9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005)mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(9.009)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

10) Lipid and membrane synthesis inhibitors, for example (10.001)propamocarb, (10.002) propamocarb hydrochloride, (10.003)tolclofos-methyl.

11) Melanin biosynthesis inhibitors, for example (11.001) tricyclazole,(11.002) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

12) Nucleic acid synthesis inhibitors, for example (12.001) benalaxyl,(12.002) benalaxyl-M (kiral-axyl), (12.003) metalaxyl, (12.004)metalaxyl-M (mefenoxam).

13) Signal transduction inhibitors, for example (13.001) fludioxonil,(13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005)quinoxyfen, (13.006) vinclozolin.

14) Compounds that can act as uncouplers, for example (14.001)fluazinam, (14.002) meptyldinocap.

15) Further compounds, for example (15.001) abscisic acid, (15.002)benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone,(15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid,(15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil,(15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014)fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenon,(15.017) mildiomycin, (15.018) natamycin, (15.019) nickeldimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021)oxamocarb, (15.022) oxathiapiprolin, (15.023) oxyfenthiin, (15.024)pentachlorophenol and salts, (15.025) phosphonic acid and salts thereof,(15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone)(15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide,(15.031)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.032)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone, (15.035)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.036)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.037)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.038)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(15.039)2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulphonate, (15.040)2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulphonate, (15.041)2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol,(15.042)2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol,(15.043)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulphonate, (15.044)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulphonate, (15.045) 2-phenylphenol and salts thereof, (15.046)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.047)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form:4-amino-5-fluoropyrimidin-2(1H)-one), (15.049)4-oxo-4-[(2-phenylethyl)amino]butyric acid, (15.050)5-amino-1,3,4-thiadiazole-2-thiol, (15.051)5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene 2-sulphonohydrazide,(15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054)9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine,(15.055) but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.056) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057)phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate,(15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulphate (2:1), (15.061)tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate.

Biological Pesticides as Mixing Components

The compounds of the formula (I) can be combined with biologicalpesticides.

Biological pesticides especially include bacteria, fungi, yeasts, plantextracts and products formed by microorganisms, including proteins andsecondary metabolites.

Biological pesticides include bacteria such as spore-forming bacteria,root-colonizing bacteria and bacteria which act as biologicalinsecticides, fungicides or nematicides.

Examples of such bacteria which are used or can be used as biologicalpesticides are:

Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacilluscereus, especially B. cereus strain CNCM 1-1562 or Bacillus firmus,strain 1-1582 (Accession number CNCM I-1582) or Bacillus pumilus,especially strain GB34 (Accession No. ATCC 700814) and strain QST2808(Accession No. NRRL B-30087), or Bacillus subtilis, especially strainGB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713(Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002(Accession No. NRRL B-50421), Bacillus thuringiensis, especially B.thuringiensis subspecies israelensis (serotype H-14), strain AM65-52(Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai,especially strain ABTS-1857 (SD-1372), or B. thuringiensis subsp.kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulusreniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomycesmicroflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), Streptomycesgalbus strain AQ 6047 (Accession Number NRRL 30232).

Examples of fungi and yeasts which are used or can be used as biologicalpesticides are:

Beauveria bassiana, in particular strain ATCC 74040, Coniothyriumminitans, in particular strain CON/M/91-8 (Accession No. DSM-9660),Lecanicillium spp., in particular strain HRO LEC 12, Lecanicilliumlecanii, (formerly known as Verticillium lecanii), in particular strainKV01, Metarhizium anisopliae, in particular strain F52 (DSM3884/ATCC90448), Metschnikowia fructicola, in particular strain NRRL Y-30752,Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particularstrain IFPC 200613, or strain Apopka 97 (Accession No. ATCC 20874),Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL89/030550), Talaromyces flavus, in particular strain V117b, Trichodermaatroviride, in particular strain SC₁ (Accession Number CBS 122089),Trichoderma harzianum, in particular T. harzianum rifai T39 (AccessionNumber CNCM I-952).

Examples of viruses which are used or can be used as biologicalpesticides are:

Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydiapomonella (codling moth) granulosis virus (GV), Helicoverpa armigera(cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua(beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV,Spodoptera littoralis (African cotton leafworm) NPV.

Also included are bacteria and fungi which are added as ‘inoculant’ toplants or plant parts or plant organs and which, by virtue of theirparticular properties, promote plant growth and plant health. Examplesinclude:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp.,Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., especiallyBurkholderia cepacia (formerly known as Pseudomonas cepacia), Gigasporaspp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillusbuchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp.,Rhizobium spp., especially Rhizobium trifolii, Rhizopogon spp.,Scleroderma spp., Suillus spp., Streptomyces spp.

Examples of plant extracts and products formed by microorganisms,including proteins and secondary metabolites, which are used or can beused as biological pesticides are:

Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassianigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin,Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza,Fungastop, Heads Up (Chenopodium quinoa saponin extract),pyrethrum/pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,“Requiem™ Insecticide”, rotenone, ryania/ryanodine, Symphytumofficinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulummajus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract,especially oilseed rape powder or mustard powder.

Safeners as Mixing Components

The compounds of the formula (I) can be combined with safeners, forexample benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide,dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim,furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalicanhydride, oxabetrinil,2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulphonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro [4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4).

Plants and Plant Parts

All plants and plant parts can be treated in accordance with theinvention. Plants are understood here to mean all plants and populationsof plants, such as desirable and undesirable wild plants or crop plants(including naturally occurring crop plants), for example cereals (wheat,rice, triticale, barley, rye, oats), maize, soya beans, potatoes, sugarbeet, sugar cane, tomatoes, bell peppers, cucumbers, melons, carrots,water melons, onions, lettuce, spinach, leeks, beans, Brassica oleracea(e.g. cabbage) and other vegetable species, cotton, tobacco, oilseedrape, and also fruit plants (the fruits being apples, pears, citrusfruits and grapes). Crop plants may be plants which can be obtained byconventional breeding and optimization methods or by biotechnologicaland genetic engineering methods or combinations of these methods,including the transgenic plants and including the plant cultivars whichare protectable or non-protectable by plant breeders' rights. Plantsshall be understood to mean all development stages such as seed,seedlings, young (immature) plants, up to and including mature plants.Plant parts shall be understood to mean all parts and organs of theplants above and below ground, such as shoot, leaf, flower and root,examples given being leaves, needles, stalks, stems, flowers, fruitbodies, fruits and seeds, and also roots, tubers and rhizomes. Plantparts also include harvested plants or harvested plant parts andvegetative and generative propagation material, for example cuttings,tubers, rhizomes, slips and seeds.

The treatment according to the invention of the plants and parts ofplants with the compounds of the formula (I) is effected directly or byallowing the compounds to act on the surroundings, the habitat or thestorage space thereof by the customary treatment methods, for example bydipping, spraying, evaporating, fogging, scattering, painting on,injecting, and, in the case of propagation material, especially in thecase of seeds, also by applying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts in accordance with the invention. In a preferred embodiment, wildplant species and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(genetically modified organisms), and parts thereof are treated. Theterm “parts” or “parts of plants” or “plant parts” has been explainedabove. Particular preference is given in accordance with the inventionto treating plants of the respective commercially customary plantcultivars or those that are in use. Plant cultivars are understood tomean plants having new properties (“traits”) and which have beenobtained by conventional breeding, by mutagenesis or by recombinant DNAtechniques. They may be cultivars, varieties, biotypes or genotypes.

Transgenic Plants, Seed Treatment and Integration Events

The preferred transgenic plants or plant cultivars (those obtained bygenetic engineering) which are to be treated in accordance with theinvention include all plants which, through the genetic modification,received genetic material which imparts particular advantageous usefulproperties (“traits”) to these plants. Examples of such properties arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to levels of water or soil salinity,enhanced flowering performance, easier harvesting, accelerated ripening,higher harvest yields, higher quality and/or higher nutritional value ofthe harvested products, better storage life and/or processability of theharvested products. Further and particularly emphasized examples of suchproperties are increased resistance of the plants against animal andmicrobial pests, such as insects, arachnids, nematodes, mites, slugs andsnails, owing, for example, to toxins formed in the plants, inparticular those formed in the plants by the genetic material fromBacillus thuringiensis (for example by the genes CryIA(a), CryIA(b),CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF andalso combinations thereof), and also increased resistance of the plantsagainst phytopathogenic fungi, bacteria and/or viruses caused, forexample, by systemic acquired resistance (SAR), systemin, phytoalexins,elicitors and resistance genes and correspondingly expressed proteinsand toxins, and also increased tolerance of the plants to certainherbicidally active compounds, for example imidazolinones,sulphonylureas, glyphosate or phosphinothricin (for example the “PAT”gene). The genes which impart the desired properties (“traits”) inquestion may also be present in combinations with one another in thetransgenic plants. Examples of transgenic plants mentioned include theimportant crop plants, such as cereals (wheat, rice, triticale, barley,rye, oats), maize, soya beans, potatoes, sugar beet, sugar cane,tomatoes, peas and other types of vegetable, cotton, tobacco, oilseedrape and also fruit plants (the fruits being apples, pears, citrusfruits and grapevines), particular emphasis being given to maize, soyabeans, wheat, rice, potatoes, cotton, sugar cane, tobacco and oilseedrape. Properties (“traits”) which are particularly emphasized are theincreased resistance of the plants to insects, arachnids, nematodes andslugs and snails.

Crop Protection—Types of Treatment

The plants and plant parts are treated with the compounds of the formula(I) directly or by action on their surroundings, habitat or storagespace using customary treatment methods, for example by dipping,spraying, atomizing, irrigating, evaporating, dusting, fogging,broadcasting, foaming, painting, spreading-on, injecting, watering(drenching), drip irrigating and, in the case of propagation material,in particular in the case of seed, additionally by dry seed treatment,liquid seed treatment, slurry treatment, by incrusting, by coating withone or more coats, etc. It is furthermore possible to apply thecompounds of the formula (I) by the ultra-low volume method or to injectthe application form or the compound of the formula (I) itself into thesoil.

A preferred direct treatment of the plants is foliar application,meaning that the compounds of the formula (I) are applied to thefoliage, in which case the treatment frequency and the application rateshould be adjusted according to the level of infestation with the pestin question.

In the case of systemically active compounds, the compounds of theformula (I) also access the plants via the root system. The plants arethen treated by the action of the compounds of the formula (I) on thehabitat of the plant. This can be accomplished, for example, bydrenching, or by mixing into the soil or the nutrient solution, meaningthat the locus of the plant (e.g. soil or hydroponic systems) isimpregnated with a liquid form of the compounds of the formula (I), orby soil application, meaning that the compounds of the formula (I)according to the invention are introduced in solid form (e.g. in theform of granules) into the locus of the plants. In the case of paddyrice crops, this can also be accomplished by metering the compound ofthe formula (I) in a solid application form (for example as granules)into a flooded paddy field.

Seed Treatment

The control of animal pests by the treatment of the seed of plants haslong been known and is the subject of constant improvements.Nevertheless, the treatment of seed entails a series of problems whichcannot always be solved in a satisfactory manner. Thus, it is desirableto develop methods for protecting the seed and the germinating plantwhich dispense with, or at least reduce considerably, the additionalapplication of pesticides during storage, after sowing or afteremergence of the plants. It is additionally desirable to optimize theamount of active ingredient used so as to provide optimum protection forthe seed and the germinating plant from attack by animal pests, butwithout damage to the plant itself by the active ingredient used. Inparticular, methods for the treatment of seed should also take accountof the intrinsic insecticidal or nematicidal properties ofpest-resistant or -tolerant transgenic plants in order to achieveoptimal protection of the seed and also the germinating plant with aminimum expenditure on pesticides.

The present invention therefore in particular also relates to a methodfor the protection of seed and germinating plants from attack by pests,by treating the seed with one of the compounds of the formula (I). Themethod according to the invention for protecting seed and germinatingplants against attack by pests further comprises a method in which theseed is treated simultaneously in one operation or sequentially with acompound of the formula (I) and a mixing component. It further alsocomprises a method where the seed is treated at different times with acompound of the formula (I) and a mixing component.

The invention likewise relates to the use of the compounds of theformula (I) for the treatment of seed for protecting the seed and theresulting plant from animal pests.

The invention further relates to seed which has been treated with acompound of the formula (I) according to the invention for protectionfrom animal pests. The invention also relates to seed which has beentreated simultaneously with a compound of the formula (I) and a mixingcomponent. The invention further relates to seed which has been treatedat different times with a compound of the formula (I) and a mixingcomponent. In the case of seed which has been treated at different timeswith a compound of the formula (I) and a mixing component, theindividual substances may be present on the seed in different layers. Inthis case, the layers comprising a compound of the formula (I) andmixing components may optionally be separated by an intermediate layer.The invention also relates to seed in which a compound of the formula(I) and a mixing component have been applied as part of a coating or asa further layer or further layers in addition to a coating.

The invention further relates to seed which, after the treatment with acompound of the formula (I), is subjected to a film-coating process toprevent dust abrasion on the seed.

One of the advantages that occur when a compound of the formula (I) actssystemically is that the treatment of the seed protects not only theseed itself but also the plants resulting therefrom, after emergence,from animal pests. In this way, the immediate treatment of the crop atthe time of sowing or shortly thereafter can be dispensed with.

A further advantage is that the treatment of the seed with a compound ofthe formula (I) can enhance germination and emergence of the treatedseed.

It is likewise considered to be advantageous that compounds of theformula (I) can especially also be used for transgenic seed.

Furthermore, compounds of the formula (I) can be employed in combinationwith compositions of signalling technology, leading to bettercolonization by symbionts such as, for example, rhizobia, mycorrhizaeand/or endophytic bacteria or fungi, and/or to optimized nitrogenfixation.

The compounds of the formula (I) are suitable for protection of seed ofany plant variety which is used in agriculture, in the greenhouse, inforests or in horticulture. More particularly, this is the seed ofcereals (for example wheat, barley, rye, millet and oats), maize,cotton, soya beans, rice, potatoes, sunflowers, coffee, tobacco, canola,oilseed rape, beets (for example sugar beets and fodder beets), peanuts,vegetables (for example tomatoes, cucumbers, beans, cruciferousvegetables, onions and lettuce), fruit plants, lawns and ornamentalplants. Of particular significance is the treatment of the seed ofcereals (such as wheat, barley, rye and oats), maize, soya beans,cotton, canola, oilseed rape, vegetables and rice.

As already mentioned above, the treatment of transgenic seed with acompound of the formula (I) is also of particular importance. Thisinvolves the seed of plants which generally contain at least oneheterologous gene which controls the expression of a polypeptide havinginsecticidal and/or nematicidal properties in particular. Theheterologous genes in transgenic seed may originate from microorganismssuch as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma,Clavibacter, Glomus or Gliocladium. The present invention isparticularly suitable for treatment of transgenic seed which comprisesat least one heterologous gene originating from Bacillus sp. Theheterologous gene is more preferably derived from Bacillusthuringiensis.

In the context of the present invention, the compound of the formula (I)is applied to the seed. The seed is preferably treated in a state inwhich it is sufficiently stable for no damage to occur in the course oftreatment. In general, the seed can be treated at any time betweenharvest and sowing. It is customary to use seed which has been separatedfrom the plant and freed from cobs, shells, stalks, coats, hairs or theflesh of the fruits. For example, it is possible to use seed which hasbeen harvested, cleaned and dried down to a moisture content whichallows storage. Alternatively, it is also possible to use seed which,after drying, has been treated with, for example, water and then driedagain, for example priming. In the case of rice seed, it is alsopossible to use seed which has been soaked, for example in water, untilit reaches a certain stage of the rice embryo (“pigeon breast stage”)which results in stimulation of germination and more uniform emergence.

When treating the seed, care must generally be taken that the amount ofthe compound of the formula (I) applied to the seed and/or the amount offurther additives is chosen in such a way that the germination of theseed is not adversely affected, or that the resulting plant is notdamaged. This has to be ensured particularly in the case of activeingredients which can exhibit phytotoxic effects at certain applicationrates.

In general, the compounds of the formula (I) are applied to the seed inthe form of a suitable formulation. Suitable formulations and processesfor seed treatment are known to the person skilled in the art.

The compounds of the formula (I) can be converted to the customaryseed-dressing formulations, such as solutions, emulsions, suspensions,powders, foams, slurries or other coating compositions for seed, andalso ULV formulations.

These formulations are prepared in a known manner, by mixing thecompounds of the formula (I) with customary additives, for examplecustomary extenders and solvents or diluents, dyes, wetting agents,dispersants, emulsifiers, antifoams, preservatives, secondarythickeners, adhesives, gibberellins, and also water.

Dyes which may be present in the seed-dressing formulations usable inaccordance with the invention are all dyes which are customary for suchpurposes. It is possible to use either pigments, which are sparinglysoluble in water, or dyes, which are soluble in water. Examples includethe dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I.Solvent Red 1.

Useful wetting agents which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are customary for the formulation ofactive agrochemical ingredients. Usable with preference are alkylnaphthalenesulphonates, such as diisopropyl or diisobutylnaphthalenesulphonates.

Suitable dispersants and/or emulsifiers which may be present in theseed-dressing formulations usable in accordance with the invention areall nonionic, anionic and cationic dispersants customary for theformulation of active agrochemical ingredients. Nonionic or anionicdispersants or mixtures of nonionic or anionic dispersants can be usedwith preference. Suitable nonionic dispersants especially includeethylene oxide/propylene oxide block polymers, alkylphenol polyglycolethers and tristyrylphenol polyglycol ethers, and the phosphated orsulphated derivatives thereof. Suitable anionic dispersants areespecially lignosulphonates, polyacrylic acid salts andarylsulphonate-formaldehyde condensates.

Antifoams which may be present in the seed-dressing formulations usablein accordance with the invention are all foam-inhibiting substancescustomary for the formulation of active agrochemical ingredients.Silicone antifoams and magnesium stearate can be used with preference.

Preservatives which may be present in the seed-dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich can be used for such purposes in agrochemical compositions.Preferred examples include cellulose derivatives, acrylic acidderivatives, xanthan, modified clays and finely divided silica.

Useful stickers which may be present in the seed-dressing formulationsusable in accordance with the invention are all customary binders usablein seed-dressing products. Preferred examples includepolyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

Gibberellins which may be present in the seed-dressing formulationsusable in accordance with the invention are preferably the gibberellinsA1, A3 (=gibberellic acid), A4 and A7; particular preference is given tousing gibberellic acid. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz- and Schadlingsbekampfungsmittel”, vol. 2,Springer Verlag, 1970, pp. 401-412).

The seed-dressing formulations usable in accordance with the inventioncan be used to treat a wide variety of different kinds of seed, eitherdirectly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats and triticale, and also the seed of maize, rice, oilseed rape,peas, beans, cotton, sunflowers, soya beans and beets, or else a widevariety of different vegetable seed. The seed-dressing formulationsusable in accordance with the invention, or the dilute use formsthereof, can also be used to dress seed of transgenic plants.

For the treatment of seed with the seed-dressing formulations usable inaccordance with the invention, or the use forms prepared therefromthrough the addition of water, all mixing units usable customarily forthe seed dressing are useful. Specifically, the procedure in seeddressing is to place the seed into a mixer in batchwise or continuousoperation, to add the particular desired amount of seed-dressingformulations, either as such or after prior dilution with water, and tomix until the formulation is distributed homogeneously on the seed. Ifappropriate, this is followed by a drying operation.

The application rate of the seed-dressing formulations usable inaccordance with the invention can be varied within a relatively widerange. It is guided by the particular content of the compounds of theformula (I) in the formulations and by the seed. The application ratesof the compound of the formula (I) are generally between 0.001 and 50 gper kilogram of seed, preferably between 0.01 and 15 g per kilogram ofseed.

Animal Health

In the animal health field, i.e. the field of veterinary medicine, thecompounds of the formula (I) are active against animal parasites, inparticular ectoparasites or endoparasites. The term “endoparasite”includes especially helminths and protozoa, such as coccidia.Ectoparasites are typically and preferably arthropods, especiallyinsects or acarids.

In the field of veterinary medicine, the compounds of the formula (I)having favourable endotherm toxicity are suitable for controllingparasites which occur in animal breeding and animal husbandry inlivestock, breeding animals, zoo animals, laboratory animals,experimental animals and domestic animals. They are active against allor specific stages of development of the parasites.

Agricultural livestock include, for example, mammals, such as sheep,goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deerand especially cattle and pigs; or poultry such as turkeys, ducks, geeseand especially chickens; or fish or crustaceans, for example inaquaculture; or, as the case may be, insects such as bees.

Domestic animals include, for example, mammals, such as hamsters, guineapigs, rats, mice, chinchillas, ferrets, and particularly dogs, cats,caged birds; reptiles, amphibians or aquarium fish.

In a specific embodiment, the compounds of the formula (I) areadministered to mammals.

In another specific embodiment, the compounds of the formula (I) areadministered to birds, namely caged birds or particularly poultry.

Use of the compounds of the formula (I) for the control of animalparasites is intended to reduce or prevent illness, cases of death andreductions in performance (in the case of meat, milk, wool, hides, eggs,honey and the like), such that more economical and simpler animalhusbandry is enabled and better animal well-being is achievable.

In relation to the field of animal health, the term “control” or“controlling” in the present context means that the compounds of theformula (I) are effective in reducing the incidence of the particularparasite in an animal infected with such parasites to an innocuousdegree. More specifically, “controlling” in the present context meansthat the compounds of the formula (I) kill the respective parasite,inhibit its growth, or inhibit its proliferation.

The arthropods include, for example, but are not limited to, from theorder of Anoplurida, for example, Haematopinus spp., Linognathus spp.,Pediculus spp., Phtirus spp. and Solenopotes spp.;

from the order of Mallophagida and the suborders Amblycerina andIschnocerina, for example, Bovicola spp., Damalina spp., Felicola spp.;Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp.,Trinoton spp., Werneckiella spp;

from the order of Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Atylotus spp.,Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culexspp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp.,Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp.,Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Luciliaspp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp.,Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp.,Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanusspp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.;

from the order of Siphonapterida, for example, Ceratophyllus spp.,Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.;

from the order of Heteropterida, for example, Cimex spp., Panstrongylusspp., Rhodnius spp., Triatoma spp.; and also nuisance and hygiene pestsfrom the order Blattarida.

In addition, in the case of the arthropods, mention should be made byway of example, without limitation, of the following Acari:

from the subclass of Acari (Acarina) and the order of Metastigmata, forexample from the family of Argasidae such as Argas spp., Ornithodorusspp., Otobius spp., from the family of Ixodidae such as Amblyomma spp.,Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp.,Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genusof multi-host ticks); from the order of Mesostigmata such as Dermanyssusspp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp.,Sternostoma spp., Tropilaelaps spp., Varroa spp.; from the order of theActinedida (Prostigmata), for example, Acarapis spp., Cheyletiella spp.,Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp.,Ornithocheyletia spp., Psorergates spp., Trombicula spp.; and from theorder of the Acaridida (Astigmata), for example, Acarus spp.,Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp.,Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp.,Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp.,Tyrophagus spp.

Examples of parasitic protozoa include, but are not limited to:

Mastigophora (Flagellata), such as:

Metamonada: from the order of Diplomonadida, for example, Giardia spp.,Spironucleus spp.

Parabasala: from the order of Trichomonadida, for example, Histomonasspp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp.,Tritrichomonas spp.

Euglenozoa: from the order of Trypanosomatida, for example, Leishmaniaspp., Trypanosoma spp.

Sarcomastigophora (Rhizopoda) such as Entamoebidae, for exampleEntamoeba spp., Centramoebidae, for example Acanthamoeba sp.,Euamoebidae, e.g. Hartmanella sp.

Alveolata such as Apicomplexa (Sporozoa): e.g. Cryptosporidium spp.;from the order of Eimeriida, for example, Besnoitia spp., Cystoisosporaspp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp.,Sarcocystis spp., Toxoplasma spp.; from the order of Adeleida, forexample, Hepatozoon spp., Klossiella spp.; from the order ofHaemosporida, for example, Leucocytozoon spp., Plasmodium spp.; from theorder of Piroplasmida, for example, Babesia spp., Ciliophora spp.,Echinozoon spp., Theileria spp.; from the order of Vesibuliferida, forexample, Balantidium spp., Buxtonella spp.

Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidiumspp., Nosema spp., and also, for example, Myxozoa spp.

The helminths that are pathogenic to humans or animals include, forexample, Acanthocephala, Nematoden, Pentastoma and Platyhelminthes (e.g.Monogenea, cestodes and trematodes).

Exemplary helminths include, but are not limited to:

Monogenea: for example: Dactylogyrus spp., Gyrodactylus spp.,Microbothrium spp., Polystoma spp., Troglecephalus spp.;

Cestodes: from the order of Pseudophyllidea, for example: Bothridiumspp., Diphyllobothrium spp., Diplogonoporus spp., Ichthyobothrium spp.,Ligula spp., Schistocephalus spp., Spirometra spp.

From the order of Cyclophyllida, for example: Andyra spp., Anoplocephalaspp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp.,Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp.,Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp.,Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephalaspp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp.,Thysanosoma spp.

Trematodes: from the class of Digenea, for example: Austrobilharziaspp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchisspp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoeliumspp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp.,Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp.,Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp.,Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeumspp., Leucochloridium spp., Metagonimus spp., Metorchis spp.,Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharziaspp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp.,Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp.,Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.

Nematodes: from the order of Trichinellida, for example: Capillariaspp., Trichinella spp., Trichomosoides spp., Trichuris spp.

From the order of Tylenchida, for example: Micronema spp.,Parastrangyloides spp., Strongyloides spp.

From the order of Rhabditina, for example: Aelurostrongylus spp.,Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonemaspp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp.,Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomumspp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp.,Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroidesspp., Globocephalus spp., Graphidium spp., Gyalocephalus spp.,Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagiaspp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirusspp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp.,Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.;Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperiaspp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp.,Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp.,Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylusspp., Syngamus spp., Teladorsagia spp., Trichonema spp.,Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp.,Uncinaria spp.

From the order of Spirurida, for example: Acanthocheilonema spp.,Anisakis spp., Ascaridia spp.; Ascanis spp., Ascarops spp., Aspiculurisspp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp.,Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.;Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp.,Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loaspp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp.,Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp.,Pseudofilaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp.,Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp.,Toxascaris spp., Toxocara spp., Wuchereria spp.

Acanthocephala: from the order of Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the order ofMoniliformida, for example: Moniliformis spp.

From the order of Polymorphida, for example: Filicollis spp.; from theorder of Echinorhynchida, for example Acanthocephalus spp.,Echinorhynchus spp., Leptorhynchoides spp.

Pentastoma: from the order of Porocephalida, for example, Linguatulaspp.

In the veterinary field and in animal husbandry, the compounds of theformula (I) are administered by methods generally known in the art, suchas via the enteral, parenteral, dermal or nasal route in the form ofsuitable preparations. Administration may be prophylactic, metaphylacticor therapeutic.

Thus, one embodiment of the present invention refers to the compounds ofthe formula (I) for use as a medicament.

A further aspect relates to the compounds of the formula (I) for use asan antiendoparasitic agent.

A further specific aspect of the invention relates to the compounds ofthe formula (I) for use as an antithelminthic agent, especially for useas a nematicide, platyxelminthicide, acanthocephalicide orpentastomicide.

A further specific aspect of the invention relates to the compounds ofthe formula (I) for use as an antiprotozoic agent.

A further aspect relates to the compounds of the formula (I) for use asan antiectoparasitic agent, especially an arthropodicide, veryparticularly an insecticide or an acaricide.

Further aspects of the invention are veterinary medicine formulationscomprising an effective amount of at least one compound of the formula(I) and at least one of the following: a pharmaceutically acceptableexcipient (e.g. solid or liquid diluents), a pharmaceutically acceptableauxiliary (e.g. surfactants), especially a pharmaceutically acceptableexcipient used conventionally in veterinary medicine formulations and/ora pharmaceutically acceptable auxiliary conventionally used inveterinary medicine formulations.

A related aspect of the invention is a method for production of aveterinary medicine formulation as described here, which comprises thestep of mixing at least one compound of the formula (I) withpharmaceutically acceptable excipients and/or auxiliaries, especiallywith pharmaceutically acceptable excipients used conventionally inveterinary medicine formulations and/or auxiliaries used conventionallyin veterinary medicine formulations.

Another specific aspect of the invention is veterinary medicineformulations selected from the group of ectoparasiticidal andendoparasiticidal formulations, especially selected from the group ofanthelmintic, antiprotozoic and arthropodicidal formulations, veryparticularly selected from the group of nematicidal,platyhelminthicidal, acanthocephalidicidal, pentastomicidal,insecticidal and acaricidal formulations, according to the aspectsmentioned, and methods for production thereof.

Another aspect relates to a method for treatment of a parasiticinfection, especially an infection caused by a parasite selected fromthe group of the ectoparasites and endoparasites mentioned here, by useof an effective amount of a compound of the formula (I) in an animal,especially a nonhuman animal, having a need therefor.

Another aspect relates to a method for treatment of a parasiticinfection, especially an infection caused by a parasite selected fromthe group of the ectoparasites and endoparasites mentioned here, by useof a veterinary medicine formulation as defined here in an animal,especially a nonhuman animal, having a need therefor.

Another aspect relates to the use of the compounds of the formula (I) inthe treatment of a parasite infection, especially an infection caused bya parasite selected from the group of the ectoparasites andendoparasites mentioned here, in an animal, especially a nonhumananimal.

In the present context of animal health or veterinary medicine, the term“treatment” includes prophylactic, metaphylactic and therapeutictreatment.

In a particular embodiment, in this way, mixtures of at least onecompound of the formula (I) with other active compounds, especially withendo- and ectoparasiticides, are provided for the field of veterinarymedicine.

In the field of animal health, “mixture” means not just that two (ormore) different active compounds are formulated in a common formulationand are correspondingly employed together, but also relates to productscomprising formulations separated for each active compound. Accordingly,when more than two active ingredients are to be employed, all activeingredients can be formulated in a common formulation or all activeingredients can be formulated in separate formulations; likewiseconceivable are mixed forms in which some of the active ingredients areformulated together and some of the active ingredients are formulatedseparately. Separate formulations allow the separate or successiveapplication of the active ingredients in question.

The active compounds specified here by their “common names” are knownand are described, for example, in the “Pesticide Manual” (see above) orcan be searched for on the Internet (e.g.: http://www.alanwood.net).

Illustrative active ingredients from the group of the ectoparasiticidesas mixing components, without any intention that this should constitutea restriction, include the insecticides and acaricides listed in detailabove. Further usable active ingredients are listed below in accordancewith the abovementioned classification based on the current IRAC Mode ofAction Classification Scheme: (1) acetylcholinesterase (AChE)inhibitors; (2) GABA-gated chloride channel blockers; (3) sodium channelmodulators; (4) nicotinic acetylcholine receptor (nAChR) competitivemodulators; (5) nicotinic acetylcholine receptor (nAChR) allostericmodulators; (6) glutamate-gated chloride channel (GluCl) allostericmodulators; (7) juvenile hormone mimetics; (8) miscellaneousnon-specific (multi-site) inhibitors; (9) chordotonal organ modulators;(10) mite growth inhibitors; (12) inhibitors of mitochondrial ATPsynthase, such as ATP disruptors; (13) uncouplers of oxidativephosphorylation via disruption of the proton gradient; (14) nicotinicacetylcholine receptor channel blockers; (15) inhibitors of chitinbiosynthesis, type 0; (16) inhibitors of chitin biosynthesis, type 1;(17) moulting disruptors (especially in Diptera); (18) ecdysone receptoragonists; (19) octopamine receptor agonists; (21) mitochondrial complexI electron transport inhibitors; (25) mitochondrial complex II electrontransport inhibitors; (20) mitochondrial complex III electron transportinhibitors; (22) voltage-dependent sodium channel blockers; (23)inhibitors of acetyl CoA carboxylase; (28) ryanodine receptormodulators; active ingredients having unknown or non-specific mechanismsof action, e.g. fentrifanil, fenoxacrim, cycloprene, chlorobenzilate,chlordimeform, flubenzimin, dicyclanil, amidoflumet, quinomethionat,triarathene, clothiazoben, tetrasul, potassium oleate, petroleum,metoxadiazone, gossyplur, flutenzine, brompropylate, cryolite;

compounds from other classes, for example butacarb, dimetilan,cloethocarb, phosphocarb, pirimiphos(-ethyl), parathion(-ethyl),methacrifos, isopropyl o-salicylate, trichlorfon, sulprofos, propaphos,sebufos, pyridathion, prothoate, dichlofenthion, demeton-S-methylsulphone, isazofos, cyanofenphos, dialifos, carbophenothion,autathiofos, aromfenvinfos(-methyl), azinphos(-ethyl),chlorpyrifos(-ethyl), fosmethilan, iodofenphos, dioxabenzofos,formothion, fonofos, flupyrazofos, fensulfothion, etrimfos;

organochlorine compounds, for example camphechlor, lindane, heptachlor;or phenylpyrazoles, e.g. acetoprole, pyrafluprole, pyriprole,vaniliprole, sisapronil; or isoxazolines, e.g. sarolaner, afoxolaner,lotilaner, fluralaner;

pyrethroids, e.g. (cis-, trans-)metofluthrin, profluthrin, flufenprox,flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin,RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin,biopermethrin, fenpyrithrin, cis-cypermethrin, cis-permethrin,clocythrin, cyhalothrin (lambda-), chlovaporthrin, or halogenatedhydrocarbon compounds (HCHs),

neonicotinoids, e.g. nithiazine

dicloromezotiaz, triflumezopyrim

macrocyclic lactones, e.g. nemadectin, ivermectin, latidectin,moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate;milbemycin oxime

triprene, epofenonane, diofenolan;

biologicals, hormones or pheromones, for example natural products, e.g.thuringiensin, codlemone or neem components

dinitrophenols, e.g. dinocap, dinobuton, binapacryl;

benzoylureas, e.g. fluazuron, penfluron,

amidine derivatives, e.g. chlormebuform, cymiazole, demiditraz

beehive varroa acaricides, for example organic acids, e.g. formic acid,oxalic acid.

Illustrative active ingredients from the group of the endoparasiticides,as mixing components, include, but are not limited to, activeanthelmintic ingredients and active antiprotozoic ingredients.

The anthelmintically active compounds include but are not limited to thefollowing nematicidally, trematicidally and/or cestocidally activecompounds:

from the class of the macrocyclic lactones, for example: eprinomectin,abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin,latidectin, milbemectin, ivermectin, emamectin, milbemycin;

from the class of the benzimidazoles and probenzimidazoles, for example:oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole,oxfendazole, netobimin, fenbendazole, febantel, thiabendazole,cyclobendazole, cambendazole, albendazole sulphoxide, albendazole,flubendazole;

from the class of the depsipeptides, preferably cyclic depsipetides,especially 24-membered cyclic depsipeptides, for example: emodepside,PF1022A;

from the class of the tetrahydropyrimidines, for example: morantel,pyrantel, oxantel;

from the class of the imidazothiazoles, for example: butamisole,levamisole, tetramisole;

from the class of the aminophenylamidines, for example: amidantel,deacylated amidantel (dAMD), tribendimidine;

from the class of the aminoacetonitriles, for example: monepantel;

from the class of the paraherquamides, for example: paraherquamide,derquantel;

from the class of the salicylanilides, for example: tribromsalan,bromoxanide, brotianide, clioxanide, closantel, niclosamide,oxyclozanide, rafoxanide;

from the class of the substituted phenols, for example: nitroxynil,bithionol, disophenol, hexachlorophen, niclofolan, meniclopholan;

from the class of the organophosphates, for example: trichlorfon,naphthalofos, dichlorvos/DDVP, crufomate, coumaphos, haloxon;

from the class of the piperazinones/quinolines, for example:praziquantel, epsiprantel;

from the class of the piperazines, for example: piperazine, hydroxyzine;

from the class of the tetracyclines, for example: tetracycline,chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline;

from various other classes, for example: bunamidine, niridazole,resorantel, omphalotin, oltipraz, nitroscanate, nitroxynil, oxamniquin,mirasan, miracil, lucanthon, hycanthon, hetolin, emetin,diethylcarbamazine, dichlorophen, diamfenetide, clonazepam, bephenium,amoscanate, clorsulon.

Active antiprotozoic ingredients include, but are not limited to, thefollowing active ingredients:

from the class of the triazines, for example: diclazuril, ponazuril,letrazuril, toltrazuril;

from the class of polyether ionophores, for example: monensin,salinomycin, maduramicin, narasin;

from the class of the macrocyclic lactones, for example: milbemycin,erythromycin;

from the class of the quinolones, for example: enrofloxacin,pradofloxacin;

from the class of the quinines, for example: chloroquin;

from the class of the pyrimidines, for example: pyrimethamine;

from the class of the sulphonamides, for example: sulfaquinoxaline,trimethoprim, sulfaclozin;

from the class of the thiamines, for example: amprolium;

from the class of the lincosamides, for example: clindamycin;

from the class of the carbanilides, for example: imidocarb;

from the class of the nitrofurans, for example: nifurtimox;

from the class of the quinazolinone alkaloids, for example:halofuginone;

from various other classes, for example: oxamniquin, paromomycin;

from the class of the vaccines or antigens from microorganisms, forexample: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimerianecatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeriaacervulina, Babesia canis vogeli, Leishmania infantum, Babesia caniscanis, Dictyocaulus viviparus.

All the mixing components mentioned, as the case may be, may also formsalts with suitable bases or acids if they are capable of doing so onthe basis of their functional groups.

Vector control

The compounds of the formula (I) can also be used in vector control. Inthe context of the present invention, a vector is an arthropod,especially an insect or arachnid, capable of transmitting pathogens, forexample viruses, worms, single-cell organisms and bacteria, from areservoir (plant, animal, human, etc.) to a host. The pathogens can betransmitted either mechanically (for example trachoma by non-stingingflies) onto a host or after injection into a host (for example malariaparasites by mosquitoes).

Examples of vectors and the diseases or pathogens they transmit are:

1) mosquitoes

-   -   Anopheles: malaria, filariasis;    -   Culex: Japanese encephalitis, filariasis, other viral diseases,        transmission of other worms;    -   Aedes: yellow fever, dengue fever, further viral disorders,        filariasis;    -   Simuliidae: transmission of worms, especially Onchocerca        volvulus;    -   Psychodidae: transmission of leishmaniasis

2) Lice: skin infections, epidemic typhus;

3) Fleas: plague, endemic typhus, tapeworms;

4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterialdiseases;

5) Mites: acariosis, epidemic typhus, rickettsialpox, tularaemia, SaintLouis encephalitis, tick-borne encephalitis (TBE), Crimean-Congohaemorrhagic fever, borreliosis;

6) Ticks: borellioses such as Borrelia bungdorferi sensu lato., Borreliaduttoni, tick-borne encephalitis, Q fever (Coxiella burnetii),babesioses (Babesia canis canis), ehrlichiosis.

Examples of vectors in the context of the present invention are insects,for example aphids, flies, leaf-hoppers or thrips, which can transmitplant viruses to plants. Other vectors capable of transmitting plantviruses are spider mites, lice, beetles and nematodes.

Further examples of vectors in the context of the present invention areinsects and arachnids such as mosquitoes, especially of the generaAedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A.dirus (malaria) and Culex, Psychodidae such as Phlebotomus, Lutzomyia,lice, fleas, flies, mites and ticks, which can transmit pathogens toanimals and/or humans.

Vector control is also possible if the compounds of the formula (I) areresistance-breaking.

Compounds of the formula (I) are suitable for use in the prevention ofdiseases and/or pathogens transmitted by vectors. Thus, a further aspectof the present invention is the use of compounds of the formula (I) forvector control, for example in agriculture, in horticulture, in forests,in gardens and in leisure facilities, and also in the protection ofmaterials and stored products.

Protection of Industrial Materials

The compounds of the formula (I) are suitable for protecting industrialmaterials against attack or destruction by insects, for example from theorders of Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera andZygentoma.

Industrial materials in the present context are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions. The use of the invention for protection of wood isparticularly preferred.

In a further embodiment, the compounds of the formula (I) are usedtogether with at least one further insecticide and/or at least onefungicide.

In a further embodiment, the compounds of the formula (I) take the formof a ready-to-use pesticide, meaning that they can be applied to thematerial in question without further modifications. Useful furtherinsecticides or fungicides especially include those mentioned above.

Surprisingly, it has also been found that the compounds of the formula(I) can be employed for protecting objects which come into contact withsaltwater or brackish water, in particular hulls, screens, nets,buildings, moorings and signalling systems, against fouling. It isequally possible to use the compounds of the formula (I), alone or incombinations with other active compounds, as antifouling agents.

Control of Animal Pests in the Hygiene Sector

The compounds of the formula (I) are suitable for controlling animalpests in the hygiene sector. More particularly, the invention can beused in the domestic protection sector, in the hygiene protection sectorand in the protection of stored products, particularly for control ofinsects, arachnids, ticks and mites encountered in enclosed spaces, forexample dwellings, factory halls, offices, vehicle cabins, animalbreeding facilities. For controlling animal pests, the compounds of theformula (I) are used alone or in combination with other active compoundsand/or auxiliaries. They are preferably used in domestic insecticideproducts. The compounds of the formula (I) are effective againstsensitive and resistant species, and against all developmental stages.

These pests include, for example, pests from the class Arachnida, fromthe orders Scorpiones, Araneae and Opiliones, from the classes Chilopodaand Diplopoda, from the class Insecta the order Blattodea, from theorders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera,Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria orOrthoptera, Siphonaptera and Zygentoma and from the class Malacostracathe order Isopoda.

Application is effected, for example, in aerosols, unpressurized sprayproducts, for example pump and atomizer sprays, automatic foggingsystems, foggers, foams, gels, evaporator products with evaporatortablets made of cellulose or plastic, liquid evaporators, gel andmembrane evaporators, propeller-driven evaporators, energy-free, orpassive, evaporation systems, moth papers, moth bags and moth gels, asgranules or dusts, in baits for spreading or bait stations.

Description of the Processes and Intermediates

The compounds of the formula (I) can be synthesized, for example,according to processes A to E, as shown in the schemes below.

Process A

Process B

Process C

Process D

Process E

Process F

Most of the organometallic compounds (e.g. aryl/hetarylboronicacids/esters, etc.) required for process A, and the catalysts needed,are commercial products or can be prepared by processes generally knownin organic chemistry.

Most of the aryl/hetaryl bromides required for process B are commercialproducts or can be prepared by processes generally known in organicchemistry.

Most of the nitrile oxides required for process C, or precursorsthereof, are commercial products or can be prepared by processesgenerally known in organic chemistry.

Most of the ortho-iodophenols required for process D are commercialproducts or can be prepared by processes generally known in organicchemistry.

The 3-aminopyridines of the formula (X) required for process F arecommercially available or can be prepared, for example, by processesknown from the literature, e.g. Liu, Zhen-Jiang; Vors, Jean-Pierre;Gesing, Ernst R. F.; Bolm, Carsten, Advanced Synthesis and Catalysis,2010, 352, 3158-3162, BAYER CROPSCIENCE AG patent: US2010/305124 A1,2010, Shafir, Alexandr; Buchwald, Stephen L., Journal of the AmericanChemical Society, 2006, 128, 8742-8743.

Amidation Process

The intermediates of the formula (IX) in process F according to theinvention can be synthesized using methods known from the literature, oranalogously to the examples explicitly mentioned.

A number of reaction conditions have been described for the amidationstep, for example G. Benz in Comprehensive Organic Synthesis, 1^(st)Ed., Pergamon Press, Oxford, 1991, Vol. 6, pp. 381-417; P. D. Bailey etal. in Comprehensive Organic Functional Group Transformation, 1st Ed.,Elsevier Science Ltd., Oxford, 1995, Vol. 5, pp. 257-308 and R.C. Larockin Comprehensive Organic Transformations, 2nd Ed., Wiley-VCH, New York,Weinheim, 1999, pp. 1929-1994. Some of these reactions proceed viaintermediate carbonyl chlorides, which can be employed in isolated formor in in-situ-generated form.

The amidation reactions are optionally carried out in the presence of acondensing agent, optionally in the presence of an acid acceptor andoptionally in the presence of a solvent.

Useful condensing agents are all the condensing agents typically usablefor such amidation reactions.

Examples include activators such as phosgene, phosphorus trichloride,phosphorus oxychloride, oxalyl chloride, oxalyl bromide or thionylchloride; carbodiimides such as N,N′-dicyclohexylcarbodiimide (DCC) and1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI), or other customarycondensing agents such as phosphorus pentoxide, polyphosphoric acid,N,N′-carbonyldiimidazole, 2-chloro-pyridine 1-methoiodide (Mukaiyama'sreagent), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ),triphenylphosphine/carbon tetrachloride, bromotripyrrolidinophosphoniumhexafluorophosphate (BROP),O-(1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphoniumhexafluorophosphate (BOP), N,N,N′,N′-bis(tetramethylene)chlorouroniumtetrafluoroborate, O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HBTU), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-bis(tetramethylene)uronium hexafluorophosphate,O-(JH-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate(TBTU), O-(JH-benzotriazol-1-yl)-N,N,N,′,N′-bis(tetramethylene)uroniumtetrafluoroborate,O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU), 1-hydroxybenzotriazole (HOBt) and4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium salt (DMT.MM),usually available as a chloride. These reagents can be used separatelyor in combination.

Suitable acid acceptors are all customary inorganic or organic bases,for example organic amines such as triethylamine, diisopropylethylamine,N-methylmorpholine, pyridine or N,N-dimethylaminopyridine, alkali metaland alkaline earth metal carbonates such as lithium carbonate, sodiumcarbonate, potassium carbonate or caesium carbonate; alkali metalbicarbonates such as sodium bicarbonate or potassium bicarbonate. Theamidation reaction in the processes according to the invention isoptionally carried out in the presence of a suitable reaction auxiliarysuch as, for example, N,N-dimethylformamide orN,N-dimethylaminopyridine. Suitable solvents or diluents are all inertorganic solvents, for example aliphatic or aromatic hydrocarbons (suchas petroleum ether, toluene, cyclohexane), halogenated hydrocarbons(such as chlorotoluene, dichlorobenzene, dichloromethane, chloroform,1,2-dichloroethane), ethers (such as diethyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane), esters (such as ethyl or methylacetate), nitrohydrocarbons (such as nitromethane, nitroethane,nitrobenzene), nitriles (such as acetonitrile, propionitrile,butyronitrile, benzonitrile), amides (such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone,hexamethylphosphoramide), and also dimethyl sulphoxide, sulpholane orwater or mixtures of the solvents mentioned.

It is also possible to use mixed anhydrides for preparation of compoundsof the formula (II) (cf. J. Am. Chem. Soc. 1967, 5012). In this process,it is possible to use chloroformic esters, for example methylchloroformate, ethyl chloroformate, isobutyl chloroformate and isopropylchloroformate. Likewise, it is possible for this purpose to usediethylacetyl chloride, trimethylacetyl chloride and similar compounds.

Processes A to F are known in principle from the prior art; accordingly,hereinbelow, literature references are only provided for the lesserknown variants:

For process B, reference is made to: Bellina, Fabio; Guazzelli, Nicola;Lessi, Marco; Manzini, Chiara; Tetrahedron, 2015, vol. 71, 2298. Thisarticle describes the B: Pd/Cu co-catalysed C—H (het)arylation.

For process D, reference is made to Vito Fiandanese et al., Tetrahedron2008, 64, 53-60. This article describes the tandem Sonogashiraoxocyclization of alkynes and ortho-iodophenols.

PREPARATION EXAMPLES

The preparation and use examples which follow illustrate the inventionwithout limiting it. The products were characterized by 1H NMRspectroscopy and/or LC-MS (Liquid Chromatography Mass Spectrometry).

The log P values were determined in accordance with OECD Guideline 117(EC Directive 92/69/EEC) by HPLC (high-performance liquidchromatography) using reversed-phase (RP) columns (C₁₈), by thefollowing methods:

[a] The LC-MS determination in the acidic range was carried out at pH2.7 with 0.1% aqueous formic acid and acetonitrile (contains 0.1% formicacid) as mobile phases; linear gradient from 10% acetonitrile to 95%acetonitrile.

[b] LC-MS determination in the neutral range was carried out at pH 7.8with 0.001 molar aqueous ammonium hydrogencarbonate solution andacetonitrile as mobile phases; linear gradient from 10% acetonitrile to95% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (having 3 to16 carbon atoms) with known log P values (log P values determined on thebasis of the retention times by linear interpolation between twosuccessive alkanones).

The NMR spectra were determined using a Bruker Avance 400 fitted with aflow probe head (60 μl volume). In individual cases, the NMR spectrawere measured with a Bruker Avance II 600.

The NMR data of selected examples are stated in classic form (8 values,multiplet splitting, number of hydrogen atoms). The splitting of thesignals was described as follows: s (singlet), d (doublet), t (triplet),q (quartet), quint (quintuplet), m (multiplet), br (for broad signals).Solvents used were CD₃CN, CDCl₃ or D6-DMSO, and tetramethylsilane (0.00ppm) was used as reference.

Process A

Example (50)

Preparation of the Compound (XI)

Step 1

1 g (4.565 mmol) of methyl 1-methyl-2-bromoimidazole-5-carboxylate(ABCR) was dissolved in 10 ml of ethanol, 5.48 ml of 1 N NaOH(aq.) wereadded and the mixture was stirred at room temperature for 60 min. Afteraddition of 5.5 ml of 1N HCl(aq.) (adjusted to pH˜3), a whiteprecipitate is formed. The mixture was concentrated to dryness and, inan ultrasonic bath, suspended in 6 ml of water. The white crystals werefiltered off and washed with 2 ml of water. The mother liquor wasconcentrated almost to dryness. The crystals were filtered off withsuction and washed with a little water. The combined crystals were driedunder oil pump vacuum. Yield: 890 mg (95% of theory).

log P[a]: 0.31;

¹H-NMR (d₆-DMSO, 400 MHz); δ=3.82 (s, 3H), 7.60 (s, 1H), 13.15 (s, ¹H)ppm.

Step 2

Using a syringe canula, about 60 mg of DMF were added to a suspension of890 mg (4.341 mmol) of 1-methyl-2-bromoimidazole-5-carboxylic acid(IX-1) in 15 ml of dichloromethane. At room temperature, 940 mg (4.341mmol) of oxalyl bromide were added, resulting in an intensive evolutionof gas. The next day, a further 10 ml of dichloromethane and 140 mg ofoxalyl bromide were added. After 1 h of stirring at room temperature, afurther 110 mg of oxalyl bromide and 30 mg of DMF were added, and themixture was stirred at room temperature for another hour, LC/MS showing96% conversion. Without further work-up, the suspension was used for thesynthesis of compound (XI-1).

Step 3 Preparation of the Compound (XI)

14.02 g (40.19 mmol) of 1-methyl-2-bromoimidazole-5-carbonyl bromide(X-1) were suspended in 80 ml of dichloromethane, and the suspension wascooled to 0° C. A solution of 4.35 g (40.19 mmol) of3-methylaminopyridine (V-1) and 41 ml (241.2 mmol) of Hünig basedissolved in 40 ml of dichloromethane was added at 0° C. The mixture wasstirred at room temperature for 1 h and then boiled under reflux for 4 hand allowed to stand at RT overnight. The mixture was concentrated underreduced pressure. The residue was taken up in 500 ml of dichloromethaneand washed 3× with a total of 400 ml of water (2× about 200 ml and 1×about 100 ml). The combined aqueous phases were extracted with about 50ml of dichloromethane and the organic phases were combined. The combinedorganic phases were washed 2× with an aqueous NaHCO₃ solution (3.5 g ofNaHCO₃ in 150 ml of water). The combined aqueous phases were extractedwith about 50 ml of dichloromethane and the organic phases werecombined, dried and concentrated under reduced pressure. Yield: 10.45 g(81.9% of theory) of a brown viscous oil in an LC/MS purity of 93%.

log P[a]: 0.65; log P[n]: 0.93

¹H-NMR (d₆-DMSO, 400 MHz); δ=3.37 (s, 3H), 3.75 (s, 3H), 6.25 (s, 1H),7.43-7.47 (m, 1H), 7.84-7.87 (m, 1H), 8.48-8.49 (m, 1H), 8.52 (m, 1H)ppm.

Preparation of the Compound (50)

A mixture of 200 mg (0.67 mmol) of bromide (XI), 141 mg (0.67 mmol) of[4-fluoro-3-(trifluorome-thyl)phenyl]boric acid, 3.8 equivalents ofsodium carbonate, 0.05 eq. of1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride, 0.05 eq. of1,1′-bis(diphenylphosphino)ferrocene, 2 ml of 1,2-dimethoxyethane and0.5 ml of water was flushed with argon and then heated in the microwaveat 140° C. with stirring for 30 minutes. The mixture was concentratedand partitioned between dichloromethane/water. The organic phase wasdried with magnesium sulphate and filtered and the filtrate wasconcentrated to dryness. The residue obtained in this manner waspurified by HPLC. Yield: 138 mg (51% of theory).

¹H-NMR (CD₃CN, 400 MHz); δ=3.43 (s, 3H), 3.83 (s, 3H), 6.39 (s, 1H),7.37-7-45 (m, 2H), 7.71-7.74 (m, 1H), 7.86-7.90 (m, 2H), 8.46-8.49 (m,2H).

Example (7)

Preparation of the Compound (7)

100 mg (0.33 mmol) of bromide (XI), 41.6 mg (0.33 mmol) ofpyridin-3-ylboric acid and 25 mg (0.03 mmol) ofbis(tricyclohexylphosphine)palladium(II) chloride were initially chargedin a mixture of degassed dioxane (2 ml) and degassed sodium carbonatesolution (2M, 1 ml), and the mixture was heated in the microwave at 120°C. for 30 min. The reaction mixture was then cooled to room temperatureand filtered through a mixture of silica gel and Extrelut® NT. Thefiltrate was concentrated to dryness. The residue was purified byRP-HPLC using a water/acetonitrile gradient as mobile phase.

¹H-NMR(400 MHz, D₆-DMSO) δ ppm: 3.42 (s, 3H), 3.87 (s, 3H), 6.42 (s,1H), 7.46-7.49 (m, 1H), 7.51-7.54 (m, 1H), 7.88-7.91 (m, 1H), 8.06-8.09(m, 1H), 8.49-8.51 (m, 1H), 8.54-8.55 (m, 1H), 8.65-8.67 (m, 1H),8.83-8.84 (m, 1H).

Example (6)

Preparation of the Compound (6)

100 mg (0.33 mmol) of bromide (XI), 41.3 mg (0.33 mmol) of phenylboricacid and 25 mg (0.03 mmol) of bis(tricyclohexylphosphine)palladium(II)chloride were initially charged in a mixture of degassed dioxane (2 ml)and degassed sodium carbonate solution (2M, 1 ml), and the mixture washeated in the microwave at 120° C. for 30 min. The reaction mixture wasthen cooled to room temperature and filtered through a mixture of silicagel and Extrelut® NT. The filtrate was concentrated to dryness. Theresidue was purified by RP-HPLC using a water/acetonitrile gradient asmobile phase.

¹H-NMR(400 MHz, D₆-DMSO) δ ppm: 3.41 (s, 3H), 3.83 (s, 3H), 6.37 (s,1H), 7.46-7.51 (m, 4H), 7.62-7.64 (m, 2H), 7.87-7.90 (m, 1H), 8.49-8.50(m, 1H), 8.54-8.55 (m, 1H).

Example (14)

Preparation of the Compound (14)

100 mg (0.33 mmol) of bromide (XI), 70.2 mg (0.33 mmol) of1-methyl-2-(4,4,5,5-tetramethyl-1.3,2-dioxaborolan-2-yl)-1H-pyrrole and25 mg (0.03 mmol) of bis(tricyclohexylphosphine)palladium(II) chloridewere initially charged in a mixture of degassed dioxane (2 ml) anddegassed sodium carbonate solution (2M, 1 ml), and the mixture washeated in the microwave at 120° C. for 30 min. The reaction mixture wasthen cooled to room temperature and filtered through a mixture of silicagel and Extrelut® NT. The filtrate was concentrated to dryness. Theresidue was purified by RP-HPLC using a water/acetonitrile gradient asmobile phase.

¹H-NMR(400 MHz, D₆-DMSO) δ ppm: 3.40 (s, 3H), 3.63 (s, 3H), 3.79 (s,3H), 6.12-6.14 (m, 1H), 6.37 (s, 1H), 6.43-6.44 (m, 1H), 6.93-6.94 (m,1H), 7.44-7.48 (m, 1H), 7.85-7.88 (m, 1H), 8.48-8.49 (m, 1H), 8.52-8.53(m, 1H).

Example (33)

Preparation of the Compound (33)

210 mg (0.71 mmol) of bromide (XI), 87 mg (0.71 mmol) ofpyridin-4-ylboric acid and 82 mg (0.07 mmol) oftetrakis(triphenylphosphine)palladium(O) were initially charged in amixture of degassed dioxane (4.3 ml) and degassed sodium carbonatesolution (2M, 3.2 ml), and the mixture was stirred at 92° C. for 14 h.The reaction mixture was then cooled to room temperature and filteredthrough Celite®. The filtrate was concentrated to dryness. The residuewas taken up in dichloromethane and water. The phases were separated.The organic phase was dried over magnesium sulphate and filtered. Thesolvent was distilled off under reduced pressure. The residue waspurified by RP-HPLC using a water/acetonitrile gradient as mobile phase.

¹H-NMR(400 MHz, D₆-DMSO) δ ppm: 3.42 (s, 3H), 3.92 (s, 3H), 6.46 (s,1H), 7.45-7.48 (m, 1H), 7.67-7.69 (m, 2H), 7.88-7.90 (m, 1H), 8.48-8.54(m, 2H), 8.68-8.70 (m, 2H).

Example (47)

Preparation of the Compound (47)

120 mg (0.40 mmol) of bromide (XI), 225 mg (0.61 mmol) of2-(tributylstannyl)pyridine, 52 mg (1.22 mmol) of lithium chloride and7.7 mg (0.04 mmol) of copper(I) iodide were initially charged indegassed dioxane (2.4 ml), and 94 mg (0.08 mmol) oftetrakis(triphenylphosphine)palladium(0) were added. Under an atmosphereof argon, the mixture was heated in the microwave at 150° C. for 60 min.The reaction mixture was then cooled to room temperature and filteredthrough Celite®. The filtrate was concentrated to dryness. The residuewas purified by column chromatography using a water/acetonitrilegradient as mobile phase.

¹H-NMR(400 MHz, D₆-DMSO) δ ppm: 3.42 (s, 3H), 4.17 (s, 3H), 6.46 (s,1H), 7.41-7.46 (m, 2H), 7.86-7.92 (m, 2H), 7.96-7.98 (m, 1H), 8.43-8.53(m, 2H), 8.65-8.66 (m, 1H).

Example (65)

Preparation of the Compound (65)

A mixture of 200 mg (0.67 mmol) of bromide (XI), 222 mg (0.81 mmol) of2-(dimethylamino)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yflnicotinonitrile,2 equivalents of potassium carbonate, 0.06 eq. of1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride, 0.8 ml ofacetonitrile and 0.2 ml of water was flushed with argon and then heatedin the microwave at 140° C. with stirring for 20 minutes. Ethyl acetatewas added and the mixture was filtered and concentrated. The residue waspurified on silica gel using dichloromethane/methanol, and via HPLC.Yield: 26 mg (10% of theory).

¹H-NMR (CD₃CN, 400 MHz); δ=3.30 (s, 6H), 3.42 (s, 3H), 3.80 (s, 3H),6.35 (s, 1H), 7.37-7-40 (m, 1H), 7.70-7.73 (m, 1H), 8.00-8.02 (m, 1H),8.44-8.49 (m, 3H).

Example (75)

Preparation of the Compound (VII-ethyl)

A mixture of 29.2 g (161 mmol) of 1-methyl-1H-imidazole-5-carbonylchloride hydrochloride (Burm et al., Heterocycles, 2001, vol. 55, #3 p.495-503), 19.7 g (161 mol) of N-ethylpyridine-3-amine and 300 ml ofpyridine was stirred under argon at 100° C. for 15 hours. After coolingto room temperature, the mixture was filtered and the filtrate wasconcentrated, 250 mmol of sodium bicarbonate were added and the mixturewas stirred in 1000 ml of ethyl acetate for 2 hours. The mixture wasfiltered again, the filtrate was concentrated and the residue waschromatographed on silica gel using ethyl acetate/methanol. Yield: 29.0g (77% of theory)

log P[n]: 0.78.

¹H-NMR (CD₃CN, 400 MHz); δ=1.15 (t, 3H), 3.80 (s, 3H), 3.88 (q, 2H),6.10 (s, 1H), 7.36-7.40 (m, 2H), 7.65-7.68 (m, 1H), 8.38 (m, 1H), 8.49(m, 1H).

Preparation of the Compound (XI-ethyl)

At −90° C. and under argon, 9.1 ml of a 2.5 molar solution ofn-butyllithium in hexane were added dropwise to a solution of 5.00 g(21.7 mmol) of VII-ethyl in 150 ml of anhydrous tetrahydrofuran over thecourse of 15 minutes. The internal temperature was kept between −85 and−90° C., and after the addition had ended, stirring was continued inthis temperature range for 10 minutes. Subsequently, at a temperaturebetween −90 and −95° C., a solution of one equivalent of1,2-dibromo-1,1,2,2-tetrachloro-ethane in 50 ml of tetrahydrofuran wasadded dropwise over a period of 10 minutes with stirring. After afurther 30 minutes at −80° C. and a further 45 minutes at −70° C., themixture was allowed to warm to room temperature over one hour. A pH of 7was established by addition of ammonium chloride, the mixture wasfiltered and the filtrate was concentrated. Chromatography on silica gelwith dichloromethane/methanol gave 4.90 g (71% of theory) of XI-ethyl.

¹H-NMR (CD₃CN, 400 MHz); δ=1.15 (t, 3H), 3.76 (s, 3H), 3.88 (q, 2H),6.17 (s, 1H), 7.36-7-39 (m, 1H), 7.65-7.68 (m, 1H), 8.38 (m, 1H), 8.49(m, 1H).

Preparation of the Compound (75)

A mixture of 115 mg (0.372 mmol) of bromide (XI-ethyl), 101 mg (0.391mmol) of2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile,2 equivalents of potassium carbonate, 0.05 equivalent of1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride, 0.8 ml ofacetonitrile and 0.2 ml of water was flushed with argon and then heatedin the microwave at 140° C. with stirring for 20 minutes.Dichloromethane was added and the mixture was filtered and concentrated.The residue was purified on silica gel using dichloromethane/methanol.Yield: 65 mg (47% of theory).

¹H-NMR (CD₃CN, 400 MHz); δ=1.18 (t, 3H), 3.81 (s, 3H), 3.92 (q, 2H),4.07 (s, 3H), 6.34 (s, 1H), 7.39-7-42 (m, 1H), 7.70-7.73 (m, 1H), 8.23(m, 1H), 8.40 (m, 1H), 8.49 (m, 1H), 8.59 (m, 1H).

Process B

Example (20)

Preparation of the Compound (XII)

12.71 g (104.7 mmol) of thionyl chloride were added to a suspension of12 g (95.2 mmol) of 1-methylimidazole-5-carboxylic acid in 72 ml oftoluene, and the mixture was stirred under reflux overnight. Thereaction mixture was concentrated under reduced pressure. A solution of10.3 g (95.2 mmol) of 3-methylaminopyridine (V-1) in 72 ml of pyridinewas added to the residue, and the resulting reaction mixture was heatedat 115° C. for 4 h. The mixture was then once more concentrated underreduced pressure and the residue was purified by column chromatographyon silica gel using the mobile phase acetonitrile/methanol 3:1. Thisgave 8.1 g (39.3% of theory) of the title compound (XV-1).

log P[n]: 0.42

¹H-NMR (CD₃CN, 400 MHz); δ=3.39 (s, 3H), 3.81 (s, 3H), 6.17 (s, 1H),7.36-7.40 (m, 2H), 7.67-7.70 (m, 1H), 8.41 (m, 1H) 8.47 (m, 1H) ppm.

Preparation of the Compound (20)

A mixture of 150 mg (0.69 mmol) of imidazole (XII), 376 mg (1.38 mmol)of 4-[(3-bromobenzyl)oxy]tetrahydro-2H-pyran, 0.05 equivalents ofpalladium(II) acetate, 2 equivalents of copper(I) iodide and 4.5 ml ofN,N-dimethylacetamide was flushed with argon and then heated in themicrowave at 160° C. with stirring for 20 minutes. The mixture was addedto 15 ml of dichloromethane and 12 ml of 10% strength sodiumthiosulphate solution and extracted 3 times with dichloromethane. Thecombined organic phases were dried over magnesium sulphate, filtered andconcentrated. The residue obtained in this manner was chromatographed onsilica gel using ethyl acetate/methanol. Yield: 110 mg (38% of theory).

¹H-NMR (CD₃CN, 400 MHz); δ=1.48-1.57 (m, 2H), 1.89-1.97 (m, 2H,superposed by solvent signal), 3.35-3.41 (m, 2H) 3.42 (s, 3H), 3.60 (m,1H), 3.82 (s, 3H), 3.82-3.88 (m, 2H), 4.60 (s, 2H), 6.37 (s, 1H),7.37-7.51 (m, 4H), 7.56 (s, 1H), 7.71-7.74 (m, 1H), 8.46-8.49 (m, 2H).

Process C

Example (71)

Preparation of the Compound (XIII)

5.00 g (23.1 mmol) of the imidazole (XII) were dissolved in 150 ml ofTHF and cooled to −90° C. During the reaction, the temperature was keptbetween −85° C. and −90° C. At −90° C., 9.68 ml (24.2 mmol) of a 2.5molar solution of n-BuLi in n-hexane were added dropwise over a periodof 30 minutes, and the mixture was stirred for another 5 minutes. 0.242g of iodine (69.4 mmol), dissolved in 50 ml of THF, was then addeddropwise over 20 minutes. The mixture was stirred at −80° C. for afurther 30 minutes and then warmed to room temperature over 1 h. Themixture was extracted with semiconcentrated sodium bicarbonatesolution/dichloromethane. The aqueous phase was extracted three moretimes with dichloromethane. The organic phases were combined, washedwith a little water, dried with sodium sulphate, filtered andconcentrated. The residue was purified on silica gel by MPLC using themobile phase ethyl acetate/methanol. Purification gave 4.35 g (55.0% oftheory).

log P[a]: 0.66; log P[n]: 0.97;

¹H-NMR (d₆-DMSO, 400 MHz); δ=3.37 (s, 3H), 3.74 (s, 3H), 6.27 (s, 1H),7.42-7.45 (m, 1H), 7.82-7.85 (m, 1H), 8.465-8.495 (m, 2H) ppm.

Preparation of the Compound (XIV)

A solution of 2.31 g (6.75 mmol) of the imidazole (XIII) and 2.34 ml(8.11 mmol) of tributyl(ethynyl)stannane in 67 ml of toluene wasdegassed with argon. 0.403 g (0.349 mmol) ofpalladiumtetrakis(triphenylphosphine) was added and the solution wasstirred under reflux for 2.5 h. The mixture was concentrated andextracted with sodium chloride solution/ethyl acetate. The organic phasewas dried with sodium sulphate, filtered and concentrated. The residuewas purified on silica gel by MPLC using the mobile phase ethylacetate/methanol. Purification gave 750 mg (45.8% of theory).

log P[a]: 0.53; log P[n]: 0.87;

¹H-NMR (CD₃CN, 400 MHz); δ=3.395 (s, 3H), 3.74 (s, 1H), 3.86 (s, 3H),6.22 (s, 1H), 7.35-7.38 (m, 1H), 7.66-7.69 (m, 1H), 8.412-8.417 (m, 1H),8.46-8.48 (m, 1H) ppm.

Preparation of the Compound (71)

A suspension of 120 mg (0.499 mmol) of the imidazole (XIV), 85.8 mg(0.549 mmol) of N-hydroxybenzenecarboximidoyl chloride and 75.9 mg(0.549 mmol) of potassium carbonate in 5.5 ml of dichloromethane wasstirred at room temperature for 16 h. The reaction was quenched withwater and extracted with dichloromethane. The organic phases werecombined, dried over sodium sulphate, filtered and concentrated. Theresidue was purified on silica gel by MPLC using the mobile phase ethylacetate/methanol. Purification gave 750 mg (45.8% of theory).

log P[a]: 1.90; log P[n]: 2.37;

¹H-NMR (d₆-DMSO, 400 MHz); δ=3.43 (s, 3H), 4.06 (s, 3H), 6.55 (s, 1H),7.44-7.48 (m, 1H), 7.53-7.57 (m, 3H), 7.60 (s, 1H), 7.87-7.91 (m, 1H),7.96-7.98 (m, 2H), 8.48-8.50 (m, 1H), 8.55-8.56 (m, 1H) ppm.

Preparation of the Compound (74)

A solution of 244 mg (3.75 mmol) of sodium azide, 31.2 mg (0.125 mmol)of copper(II) sulphate pentahydrate, 58.1 mg (0.293 mmol) of sodiumL-ascorbate and 0.058 ml (0.936 mmol) of methyl iodide in 9 ml ofdimethyl sulphoxide and 1 ml of water was stirred at room temperaturefor 10 min. 150 mg (0.624 mmol) of2-ethynyl-N,1-dimethyl-N-(pyridin-3-yl)-1H-imidazole-5-carboxamide (C)were added and the solution was stirred at room temperature for 16 h.The mixture was diluted with water, made basic (pH=8) with concentratedsodium bicarbonate solution and extracted three times with ethylacetate. The organic phases were combined, washed three times withwater, dried with sodium sulphate, filtered and concentrated. Theresidue was purified on RP18 by HPLC using the mobile phaseacetonitrile/water. Purification gave 38.0 mg (20.5% of theory).

log P[a]: 0.27; log P[n]: 0.76;

¹H-NMR (d6-DMSO, 400 MHz); δ=3.41 (s, 3H), 4.09 (s, 3H), 4.10 (s, 3H),6.36 (s, 1H), 7.43-7.46 (m, 1H), 7.85-7.88 (m, 1H), 8.46-8.48 (m, 2H),8.53-8.54 (m, 1H) ppm.

Process D

Preparation of the Compound (70)

A solution of 100 mg (0.416 mmol) of the imidazole (XIV) and 45.8 mg(0.208 mmol) of 2-iodophenol in 1 ml of THF and 2 ml of triethylaminewas degassed with argon. 7.3 mg (0.010 mmol) ofdichlorobis(triphenylphosphine)palladium and 3.4 mg (0.021 mmol) ofcopper iodide were added and the solution was stirred at 50° C. for 6 h.The mixture was extracted with ammonium chloride solution/ethyl acetate.The aqueous phase was extracted two more times with ethyl acetate. Theorganic phases were combined, washed three times with water, dried withsodium sulphate, filtered and concentrated. The residue was purified onsilica gel by MPLC using the mobile phase ethyl acetate/methanol.Purification gave 13.0 mg (9.4% of theory).

log P[a]: 1.63; log P[n]: 1.87;

¹H-NMR (d₆-DMSO, 400 MHz); δ=3.43 (s, 3H), 4.07 (s, 3H), 6.48 (s, 1H),7.30-7.34 (m, 1H), 7.38-7.42 (m, 2H), 7.44-7.48 (m, 1H), 7.65-7.67 (m,1H), 7.72-7.74 (m, 1H), 7.87-7.90 (m, 1H), 8.48-8.49 (m, 1H), 8.54-8.55(m, 1H) ppm.

Process E

Example (2)

Preparation of the Compound (XVI)

2 g (6.59 mmol) of 5-bromo-4-fluoro-2-methylphenyl-2,2,2-trifluoroethylsulphide (US2015/344499 A1, p. 64), 1.76 g (6.92 mmol) ofbis(pinacolato)diboron, 162 mg (0.19 mmol) of[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride, 110 mg(0.19 mmol) of 1,1′-bis(diphenylphosphino)ferrocene and 1.94 g (19.7mmol) of potassium acetate were initially charged in degassed dioxane(29 ml) and heated at boiling point for 6 h. The reaction mixture wasthen cooled to room temperature and concentrated under reduced pressure,and the residue was taken up in dichloromethane. The organic phase waswashed with water, dried over magnesium sulphate and filtered. Themixture was dissolved in ethyl acetate and filtered through silica geland the solvent was distilled off under reduced pressure. The residuewas purified by column chromatography using a cyclohexane/acetonegradient as mobile phase.

log P (acidic/neutral): 4.89/4.80; MH⁺351; ¹H-NMR(400 MHz, D₆-DMSO) δppm: 1.29 (s, 12H), 2.46 (s, 3H), 3.79 (q, 2H), 7.17 (d, 1H), 7.77 (d,1H).

Preparation of the Compound (XVIII)

250 mg (1.14 mmol) of the bromide (ABCR), 400 mg (1.14 mmol) of2-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneand 39 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium(0) wereinitially charged in a mixture of degassed acetonitrile (4 ml) anddegassed sodium carbonate solution (1M, 5 ml), and the mixture wasstirred at 72° C. for 14 h. The reaction mixture was then cooled to roomtemperature and concentrated under reduced pressure, and the residue wastaken up in dichloromethane. The organic phase was washed with water,dried over magnesium sulphate and filtered. The solvent was distilledoff under reduced pressure and the residue was purified by columnchromatography purification using a cyclohexane/acetone gradient asmobile phase.

log P (acidic/neutral): 3.09/3.19; MH⁺: 363; ¹H-NMR(400 MHz, D₆-DMSO) δppm: 2.46 (s, 3H), 3.71 (s, 3H), 3.83 (s, 3H), 3.99 (q, 2H), 7.42 (d,1H), 7.75 (d, 1H), 7.81 (s, 1H).

Preparation of the Compound (XIX)

50.5 mg (0.13 mmol) of methyl2-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-1-methyl-1H-imidazole-5-carboxylatewere initially charged in a mixture of tetrahydrofuran (0.8 ml) andwater (0.8 ml), and the solution was cooled to 0° C. 6.7 mg (0.27 mmol)of lithium hydroxide were then added, and the mixture was stirred atroom temperature for 14 h. The organic solvent was distilled off underreduced pressure and the aqueous solution was adjusted to pH=3 using 1NHCl. The product precipitated as a solid. The latter was filtered offwith suction and dried.

log P (acidic/neutral): 1.83/0.95; MH⁺: 349; ¹H-NMR(400 MHz, D₆-DMSO) δppm: 2.47 (s, 3H), 3.69 (s, 3H), 4.00 (q, 2H), 7.41 (d, 1H), 7.73-7.75(m, 2H).

Example (2)

Preparation of the Compound (2)

28 mg (0.08 mmol) of the carboxylic acid (XIX) were initially charged indioxane (0.5 ml), and 18.5 mg (0.09 mmol) of EDCI were added. Themixture was stirred at room temperature for 1 h. 8.7 mg (0.08 mmol) ofN-methylpyridine-3-amine (XX), dissolved in dioxane (0.5 ml), were thenadded, and the mixture was stirred at room temperature for 14 h. Thereaction mixture was concentrated under reduced pressure and the residuewas taken up in water and ethyl acetate. The phases were separated andthe aqueous phase was extracted twice with ethyl acetate. The combinedorganic phases were dried over magnesium sulphate and filtered. Theresidue was purified by column chromatography using a cyclohexane/ethylacetate gradient as mobile phase.

log P (acidic/neutral): 2.23/2.48; MH⁺: 439; ¹H-NMR(400 MHz, D₆-DMSO) δppm: 2.45 (s, 3H), 3.41 (s, 3H), 3.65 (s, 3H), 3.98 (q, 2H), 6.39 (s,1H), 7.37 (d, 1H), 7.47-7.50 (m, 1H), 7.66 (d, 1H), 7.89-7.92 (m, 1H),8.50-8.56 (m, 2H)

Table 1

Compounds of the Formula (II)

in which the substituents have the meanings indicated in the table(Y=methyl, W═V=hydrogen, Q=O, T=electron pair):

The abbreviation “na” means that there were no corresponding values.

logp- logp- Example no. X A neutral acidic  1

Methyl 2.21 1.72  2

Methyl 2.48 2.23  3

Methyl 1.75 1.24  4

Methyl 0.73 0.35  5

Methyl 1.43 1.07  6

Methyl na 0.58  7

Methyl na 0.18  8

Methyl na 1.16  9

Methyl na 1.10  10

Methyl na 1.29  11

Methyl na 1.23  12

Methyl na 1.66  13

Methyl na 1.79  14

Methyl na 0.62  15

Methyl na 0.29  16

Methyl na 0.99  17

Methyl 2.28 2.00  18

Methyl 2.36 1.87  19

Methyl 1.43 0.86  20

Methyl 1.57 1.11  22

Methyl 1.08 0.75  23

Methyl 2.03 1.43  24

Methyl 1.49 1.07  25

Methyl 1.68 1.21  26

Methyl 1.70 1.19  27

Methyl 1.89 1.35  28

Methyl 1.95 1.56  29

Methyl 1.55 1.04  30

Methyl 2.05 1.57  41

Methyl 1.70 1.18  42

Methyl 2.02 1.80  43

Methyl na 1.44  44

Methyl 1.81 1.39  45

Methyl 1.86 1.28  46

Methyl 1.35 0.73  47

Methyl 1.16 0.74  48

Methyl 1.65 1.22  49

Methyl 1.62 1.28  50

Methyl 2.08 1.72  51

Methyl 2.43 2.17  52

Methyl 1.99 1.64  53

Methyl 2.63 2.43  54

Methyl 2.14 1.90  55

Methyl 1.92 1.72  56

Methyl 1.96 na  57

Methyl 2.40 2.09  58

Methyl 1.33 0.91  59

Methyl 1.69 1.42  60

Methyl 1.52 1.21  61

Methyl 1.96 1.85  62

Methyl 1.37 0.78  63

Methyl 1.52 1.15  64

Methyl 0.98 0.75  65

Methyl 1.50 1.10  66

Methyl 1.45 1.16  67

Methyl 1.73 1.50  68

Methyl 1.44 1.20  69

Methyl 1.74 1.52  70

Methyl 1.87 1.63  71

Methyl 1.99 1.9   72

Methyl 1.51 1.42  73

Methyl 1.24 0.88  74

Methyl 0.76 0.27  75

Ethyl 1.65 1.46  76

Ethyl 1.95 1.69  77

Ethyl 1.39 0.97  78

Methyl 1.6  1.23  79

Methyl 0.7   80

Methyl 1.62 0.97  81

Methyl 1.69 0.89  82

Methyl 1.45 0.65  83

Methyl 1.44 0.9   84

Methyl 1.54 0.8   85

Methyl 0.9   86

Methyl 2.04 1.91  87

Methyl 1.64 1.35  88

Methyl 1.16 0.53  89

Methyl 1.53 0.93  90

Methyl 1.68 1.28  91

Methyl 1.33 0.93  92

Methyl 1.43 0.8   93

Methyl 1.28 0.66  94

Methyl 1.26 1    95

Methyl 2   1.75  96

Methyl 1.53 1.2   97

Methyl 1.67 1.37  98

Methyl 1.59 1.14  99

Methyl 2.23 2.05 100

Methyl 1.57 1.34 101

Methyl 1.38 0.91 102

Methyl 1.79 1.21 103

Methyl 1.25 0.58 104

Methyl 1.03 0.23 105

Methyl 1.87 1.55 106

Methyl 1.1  0.75

Table 2

NMR Data of Selected Examples

NMR Peak List Method

The 1H-NMR data of selected examples are noted in the form of 1H-NMRpeak lists. For each signal peak, first the 6 value in ppm and then thesignal intensity in round brackets are listed. The δ value—signalintensity number pairs for different signal peaks are listed withseparation from one another by semicolons.

The peak list for one example therefore has the form:

δ1 (intensity 1); δ2 (intensity 2); . . . ; δi (intensity i); . . . ; δn(intensity n)

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and the relative intensity thereof may beshown in comparison to the most intense signal in the spectrum.

Calibration of the chemical shift of 1H NMR spectra is accomplishedusing tetramethylsilane and/or the chemical shift of the solvent,particularly in the case of spectra which are measured in DMSO.Therefore, the tetramethylsilane peak may but need not occur in NMR peaklists.

The lists of the 1H-NMR peaks are similar to the classic 1H-NMR printsand thus usually comprise all peaks listed in a classic NMRinterpretation.

In addition, like classic 1H-NMR prints, they may show solvent signals,signals of stereoisomers of the target compounds, which are likewise thesubject matter of the invention, and/or peaks of impurities.

When stating compound signals in the delta range of solvents and/orwater, in our lists of 1H NMR peaks, the usual solvent peaks, forexample peaks of DMSO in DMSO-D6 and the peak of water are shown, whichusually have on average a high intensity.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in identifyingreproduction of our preparation process with reference to “by-productfingerprints”.

An expert calculating the peaks of the target compounds by known methods(MestreC, ACD simulation, but also with empirically evaluated expectedvalues) can, if required, isolate the peaks of the target compounds,optionally using additional intensity filters. This isolation would besimilar to the relevant peak picking in classic 1H-NMR interpretation.

Further details of 1H NMR peak lists can be found in the ResearchDisclosure Database Number 564025.

TABLE 2 Analytical NMR data for the compounds listed in Table 1: 11H-NMR(400.0 MHz, DMSO): δ = 8.544(2.6); 8.538(2.6); 8.504(1.7);8.500(1.9); 8.492(1.9); 8.489(1.9); 7.926(0.5); 7.919(0.5); 7.908(1.0);7.905(1.2); 7.902(1.2); 7.898(1.0); 7.888(1.1); 7.884(1.3); 7.882(1.3);7.878(1.1); 7.755(0.4); 7.740(3.1); 7.600(1.3); 7.580(1.7); 7.539(1.2);7.519(2.3); 7.489(3.5); 7.477(1.6); 7.469(3.7); 7.456(1.4); 7.450(1.0);6.374(3.6); 5.758(1.5); 4.139(1.0); 4.113(3.1); 4.087(3.2); 4.061(1.1);3.878(0.4); 3.833(16.0); 3.412(15.3); 3.333(29.7); 2.687(1.9);2.674(2.0); 2.507(26.6); 2.503(34.4); 2.499(26.4); 1.352(1.0);1.337(0.4); 1.259(0.4); 1.249(0.6); 1.234(1.4); 0.000(5.7) 21H-NMR(400.0 MHz, DMSO): δ = 8.559(3.2); 8.552(3.2); 8.517(2.2);8.514(2.3); 8.505(2.3); 8.502(2.2); 8.317(0.5); 7.920(1.3); 7.916(1.6);7.910(1.2); 7.899(1.4); 7.896(1.6); 7.890(1.3); 7.673(3.0); 7.655(2.9);7.502(1.8); 7.490(1.8); 7.481(1.7); 7.470(1.6); 7.388(2.7); 7.361(2.6);6.896(0.8); 6.718(0.5); 6.390(4.0); 4.014(1.2); 3.988(3.9); 3.974(0.8);3.962(4.0); 3.936(1.4); 3.653(11.3); 3.649(11.0); 3.407(20.0);3.374(0.4); 3.329(196.1); 2.735(0.3); 2.676(1.2); 2.672(1.5);2.667(1.2); 2.556(0.6); 2.507(170.2); 2.502(215.1); 2.498(160.2);2.449(16.0); 2.334(1.1); 2.329(1.4); 2.325(1.1); 1.351(7.3); 1.336(2.9);1.314(0.5); 1.298(1.4); 1.259(2.4); 1.250(4.4); 1.230(9.2); 1.140(0.5);0.868(0.6); 0.852(1.2); 0.836(0.7); 0.000(10.9) 3 1H-NMR(400.0 MHz,CD₃CN): δ = 8.484(1.3); 8.481(1.3); 8.472(1.4); 8.469(1.4); 8.460(1.9);8.454(1.9); 7.739(0.8); 7.735(0.9); 7.733(0.9); 7.729(0.7); 7.718(0.9);7.715(1.0); 7.712(1.0); 7.708(0.8); 7.440(2.3); 7.419(0.6); 7.408(1.2);7.399(1.6); 7.387(1.2); 7.381(2.2); 7.376(1.1); 7.360(2.1); 7.355(2.1);7.349(2.0); 7.344(1.2); 7.339(1.0); 7.335(0.9); 7.331(1.0); 7.328(0.7);6.371(3.3); 3.945(0.3); 3.820(15.3); 3.425(15.6); 2.958(15.3);2.827(12.7); 2.503(16.0); 2.174(45.5); 1.973(13.8); 1.964(1.2);1.957(2.3); 1.952(11.7); 1.946(17.6); 1.940(23.3); 1.934(16.1);1.927(8.4); 1.821(0.3); 1.270(0.6); 0.007(2.2); 0.000(46.8); −0.008(2.2)4 1H-NMR(400.0 MHz, DMSO): δ = 8.939(5.8); 8.927(5.9); 8.537(1.9);8.532(2.0); 8.482(1.4); 8.478(1.6); 8.470(1.5); 8.466(1.6); 7.898(0.8);7.894(0.9); 7.892(0.9); 7.888(0.8); 7.878(0.9); 7.874(1.0); 7.871(1.0);7.868(0.8); 7.549(1.6); 7.536(3.1); 7.524(1.5); 7.470(1.0); 7.468(1.0);7.458(1.1); 7.456(1.0); 7.449(1.0); 7.448(1.0); 7.437(0.9); 7.436(0.9);6.501(1.9); 5.757(0.4); 4.086(16.0); 3.427(15.1); 3.411(0.6);3.345(44.0); 2.672(0.4); 2.668(0.3); 2.526(1.1); 2.521(1.7);2.512(25.0); 2.508(52.2); 2.503(69.3); 2.499(50.5); 2.494(24.9);2.330(0.4); 2.325(0.3); 0.146(0.4); 0.008(3.3); 0.000(97.7);−0.009(3.9); −0.150(0.4) 5 1H-NMR(400.0 MHz, DMSO): δ = 8.549(3.2);8.545(3.2); 8.500(2.2); 8.497(2.2); 8.489(2.4); 8.485(2.0); 8.141(3.6);8.026(3.9); 7.907(1.8); 7.903(1.8); 7.888(3.9); 7.877(3.2); 7.873(2.8);7.868(2.8); 7.772(1.8); 7.752(2.5); 7.733(1.0); 7.488(1.5); 7.476(1.6);7.468(1.6); 7.456(1.3); 6.411(3.8); 5.754(1.7); 4.277(0.6); 4.268(0.5);4.241(1.3); 4.214(1.5); 4.192(1.4); 4.166(1.4); 4.140(0.5); 4.130(0.6);3.878(16.0); 3.419(15.5); 3.388(0.7); 3.319(13.1); 2.671(1.0);2.506(133.1); 2.502(151.4); 2.328(1.0); 0.146(0.4); 0.000(86.6);−0.150(0.5) 6 1H-NMR(400.0 MHz, DMSO): δ = 8.547(1.8); 8.546(1.9);8.541(2.0); 8.502(1.4); 8.498(1.5); 8.490(1.6); 8.487(1.5); 7.904(0.8);7.900(1.0); 7.897(0.9); 7.894(0.9); 7.884(1.0); 7.880(1.1); 7.877(1.1);7.873(0.9); 7.641(1.8); 7.634(1.4); 7.630(1.2); 7.621(2.6); 7.617(2.3);7.509(0.7); 7.505(0.6); 7.497(2.3); 7.492(1.7); 7.489(2.2); 7.483(3.9);7.479(4.3); 7.471(1.1); 7.468(1.4); 7.467(1.4); 7.456(1.1); 7.455(1.0);6.366(3.2); 3.831(16.0); 3.411(15.0); 3.359(0.4); 3.327(134.9);3.301(0.4); 2.671(0.3); 2.541(21.9); 2.524(0.8); 2.519(1.2);2.511(19.4); 2.506(40.1); 2.502(53.5); 2.497(40.0); 2.493(20.2);2.328(0.4); 0.000(1.0) 7 1H-NMR(400.0 MHz, DMSO): δ = 20.010(0.4);8.839(1.7); 8.835(1.7); 8.666(1.2); 8.662(1.4); 8.654(1.4); 8.650(1.4);8.548(1.7); 8.542(1.9); 8.505(1.3); 8.501(1.6); 8.493(1.5); 8.490(1.5);8.089(0.7); 8.084(1.1); 8.079(0.8); 8.069(0.9); 8.064(1.2); 8.059(0.9);7.910(0.7); 7.906(0.9); 7.900(0.8); 7.889(0.9); 7.886(1.0); 7.883(1.1);7.879(0.9); 7.539(1.0); 7.527(1.0); 7.520(1.0); 7.507(0.9); 7.489(1.1);7.477(1.1); 7.468(1.1); 7.456(1.0); 6.418(2.6); 3.865(16.0);3.415(14.7); 3.370(1.3); 3.326(1758.5); 3.240(1.0); 2.675(3.3);2.670(4.5); 2.666(3.4); 2.541(9.4); 2.524(11.3); 2.519(16.9);2.510(240.7); 2.506(501.5); 2.501(671.4); 2.497(490.9); 2.492(236.5);2.333(3.1); 2.328(4.3); 2.324(3.2); 2.289(0.4); 1.236(0.5); 0.000(13.4)8 1H-NMR(400.0 MHz, DMSO): δ = 8.531(1.5); 8.525(1.6); 8.497(1.1);8.493(1.2); 8.485(1.2); 8.481(1.2); 7.892(0.7); 7.889(0.8); 7.886(0.8);7.882(0.7); 7.872(0.8); 7.868(0.9); 7.866(0.9); 7.862(0.7); 7.483(0.9);7.481(0.9); 7.471(0.9); 7.469(0.9); 7.462(0.8); 7.461(0.8); 7.450(0.8);7.449(0.8); 7.216(3.6); 7.101(1.6); 6.333(2.8); 3.810(12.3);3.404(11.6); 3.342(0.6); 3.323(109.8); 2.670(0.4); 2.541(21.6);2.524(0.9); 2.510(22.1); 2.506(44.1); 2.501(57.7); 2.497(42.5);2.492(21.1); 2.333(0.4); 2.316(16.0); 0.000(1.1) 9 1H-NMR(400.0 MHz,DMSO): δ = 8.544(2.2); 8.539(2.2); 8.509(1.6); 8.506(1.7); 8.497(1.7);8.494(1.6); 7.891(0.9); 7.887(1.1); 7.885(1.0); 7.881(0.9); 7.871(1.0);7.867(1.2); 7.864(1.2); 7.861(1.0); 7.633(1.2); 7.614(2.3); 7.580(0.8);7.574(0.9); 7.564(1.2); 7.558(1.3); 7.553(0.6); 7.544(0.7); 7.537(0.8);7.490(1.6); 7.478(1.6); 7.474(2.2); 7.471(3.0); 7.462(3.0); 7.456(4.0);7.444(0.6); 6.393(2.7); 3.565(16.0); 3.410(15.2); 3.384(0.8);3.324(662.6); 3.269(0.7); 3.252(0.5); 2.994(0.3); 2.675(1.7);2.670(2.3); 2.666(1.8); 2.541(60.2); 2.510(144.7); 2.506(273.9);2.501(355.6); 2.497(273.5); 2.493(150.3); 2.367(0.3); 2.332(1.7);2.328(2.3); 2.324(1.8); 0.000(6.2) 10 1H-NMR(400.0 MHz, DMSO): δ =8.537(1.9); 8.532(2.0); 8.500(1.5); 8.496(1.6); 8.488(1.6); 8.484(1.5);7.899(0.8); 7.895(1.0); 7.892(0.9); 7.888(0.9); 7.878(0.9); 7.875(1.0);7.872(1.0); 7.868(0.9); 7.692(2.2); 7.687(1.5); 7.633(0.7); 7.629(1.2);7.624(0.7); 7.616(1.0); 7.612(1.5); 7.607(1.0); 7.560(0.6); 7.555(0.4);7.544(1.7); 7.540(3.2); 7.538(2.7); 7.536(2.6); 7.519(1.5); 7.500(0.4);7.484(1.1); 7.482(1.1); 7.472(1.1); 7.471(1.1); 7.464(1.0); 7.462(1.0);7.452(1.0); 7.450(1.0); 6.392(2.9); 3.851(16.0); 3.411(14.8);3.325(238.3); 3.301(0.6); 2.675(0.5); 2.671(0.6); 2.666(0.5);2.541(35.4); 2.524(1.5); 2.519(2.4); 2.511(36.5); 2.506(75.8);2.501(101.6); 2.497(74.6); 2.492(36.3); 2.473(0.4); 2.333(0.5);2.328(0.7); 2.324(0.5); 0.000(2.2) 11 1H-NMR(400.0 MHz, DMSO): δ =8.541(1.9); 8.535(2.0); 8.498(1.5); 8.494(1.6); 8.486(1.6); 8.482(1.5);7.899(0.8); 7.896(0.9); 7.893(0.9); 7.889(0.8); 7.879(0.9); 7.875(1.0);7.872(1.0); 7.869(0.9); 7.689(0.4); 7.682(3.2); 7.677(1.2); 7.666(1.4);7.661(4.7); 7.655(0.7); 7.569(0.6); 7.563(4.7); 7.558(1.4); 7.546(1.1);7.541(3.2); 7.483(1.1); 7.482(1.1); 7.471(1.1); 7.470(1.1); 7.463(1.0);7.462(1.0); 7.451(1.0); 7.450(1.0); 6.377(3.2); 3.834(16.0);3.408(15.1); 3.365(0.5); 3.325(446.9); 3.291(0.6); 2.679(0.5);2.675(1.0); 2.670(1.4); 2.666(1.0); 2.662(0.5); 2.541(41.6); 2.524(3.2);2.519(4.9); 2.510(76.1); 2.506(156.4); 2.501(207.5); 2.497(152.7);2.492(74.8); 2.337(0.5); 2.333(0.9); 2.328(1.3); 2.324(1.0); 0.000(2.6)12 1H-NMR(400.0 MHz, DMSO): δ = 20.009(0.6); 8.539(1.9); 8.533(2.0);8.501(1.5); 8.492(1.6); 8.489(1.6); 7.879(1.0); 7.865(1.0); 7.861(1.1);7.855(1.0); 7.827(2.7); 7.821(2.9); 7.576(1.2); 7.571(1.2); 7.555(2.1);7.550(2.2); 7.505(3.6); 7.484(3.1); 7.472(1.2); 7.464(1.1); 7.452(1.1);6.407(2.5); 3.834(0.4); 3.571(16.0); 3.408(15.0); 3.371(1.1);3.324(2480.1); 3.228(1.3); 3.187(0.8); 2.994(0.5); 2.675(5.0);2.670(6.8); 2.666(5.0); 2.541(36.7); 2.524(17.1); 2.510(384.4);2.506(771.9); 2.501(1012.5); 2.497(743.1); 2.492(363.2); 2.332(4.7);2.328(6.5); 2.323(4.8); 2.288(0.5); 1.235(0.8); 0.000(17.7) 131H-NMR(400.0 MHz, DMSO): δ = 8.536(2.5); 8.530(2.6); 8.497(1.8);8.494(1.8); 8.486(1.8); 8.483(1.8); 7.909(3.1); 7.905(3.2); 7.898(1.2);7.894(1.3); 7.888(1.0); 7.877(1.1); 7.873(1.3); 7.868(1.0); 7.765(2.3);7.744(3.5); 7.665(2.1); 7.660(2.0); 7.644(1.4); 7.639(1.4); 7.481(1.4);7.469(1.4); 7.461(1.3); 7.449(1.3); 6.403(3.4); 3.862(16.0);3.410(15.3); 3.325(107.4); 3.286(0.4); 2.671(0.4); 2.541(13.6);2.506(46.9); 2.502(58.1); 2.329(0.3); 0.000(0.9) 14 1H-NMR(400.0 MHz,DMSO): δ = 8.530(1.9); 8.525(1.9); 8.491(1.4); 8.488(1.5); 8.480(1.5);8.476(1.5); 7.884(0.8); 7.880(0.9); 7.877(0.9); 7.874(0.8); 7.864(0.9);7.860(1.0); 7.857(1.0); 7.853(0.9); 7.477(1.0); 7.476(1.1); 7.465(1.0);7.464(1.1); 7.457(1.0); 7.455(1.0); 7.445(1.0); 7.443(1.0); 6.936(1.3);6.931(1.7); 6.930(1.7); 6.925(1.4); 6.442(1.5); 6.438(1.6); 6.433(1.8);6.428(1.7); 6.373(3.6); 6.139(1.7); 6.132(1.9); 6.129(1.8); 6.123(1.6);3.789(16.0); 3.629(15.1); 3.401(15.3); 3.381(0.4); 3.371(0.4);3.325(392.9); 3.286(0.5); 2.675(0.9); 2.670(1.2); 2.666(0.9);2.661(0.5); 2.541(42.4); 2.524(3.1); 2.519(4.8); 2.510(66.5);2.506(137.3); 2.501(183.9); 2.497(137.6); 2.492(70.3); 2.337(0.4);2.333(0.9); 2.328(1.2); 2.324(0.9); 2.319(0.4); 0.000(3.2) 151H-NMR(400.0 MHz, DMSO): δ = 8.518(1.9); 8.512(2.0); 8.478(1.4);8.474(1.5); 8.466(1.5); 8.462(1.5); 8.216(2.0); 8.214(2.5); 8.212(2.5);8.210(2.0); 7.877(0.8); 7.873(0.9); 7.870(0.9); 7.866(0.8); 7.856(0.9);7.852(1.0); 7.850(1.0); 7.846(0.9); 7.805(1.8); 7.800(2.8); 7.796(1.7);7.464(1.1); 7.462(1.1); 7.452(1.1); 7.450(1.0); 7.443(1.0); 7.431(1.0);6.848(2.0); 6.846(2.2); 6.844(2.2); 6.842(2.1); 6.310(3.4); 3.855(16.0);3.396(15.1); 3.360(0.4); 3.326(206.1); 2.675(0.4); 2.670(0.5);2.666(0.4); 2.541(39.8); 2.524(1.2); 2.510(32.1); 2.506(65.9);2.501(87.8); 2.497(64.8); 2.492(32.0); 2.333(0.4); 2.328(0.6);2.324(0.4); 0.000(1.5) 16 1H-NMR(400.0 MHz, DMSO): δ = 8.527(1.9);8.521(2.0); 8.495(1.4); 8.492(1.6); 8.483(1.5); 8.480(1.6); 7.881(0.8);7.877(0.9); 7.874(0.9); 7.871(0.9); 7.860(0.9); 7.857(1.0); 7.854(1.1);7.850(1.0); 7.478(1.1); 7.466(1.1); 7.458(1.1); 7.446(1.0); 6.814(2.4);6.812(2.5); 6.333(3.4); 3.674(16.0); 3.397(15.2); 3.381(0.4);3.357(0.8); 3.327(636.7); 3.278(0.7); 3.256(0.4); 2.994(0.3);2.675(1.0); 2.671(1.4); 2.666(1.1); 2.541(44.3); 2.524(3.3); 2.519(5.0);2.511(77.2); 2.506(160.7); 2.502(216.1); 2.497(159.8); 2.492(79.3);2.402(8.3); 2.333(1.0); 2.328(1.4); 2.324(1.0); 2.271(10.6); 0.000(4.2)17 1H-NMR(400.0 MHz, DMSO): δ = 8.549(2.3); 8.544(2.2); 8.504(1.6);8.500(1.7); 8.492(1.7); 8.488(1.7); 7.972(2.4); 7.909(1.8); 7.906(2.4);7.889(2.3); 7.885(2.7); 7.883(2.3); 7.879(1.3); 7.838(1.1); 7.819(1.4);7.691(1.6); 7.671(2.6); 7.652(1.1); 7.488(1.2); 7.477(1.2); 7.468(1.2);7.456(1.1); 6.429(2.6); 3.864(16.0); 3.418(15.4); 3.360(5.3);2.944(0.8); 2.784(0.6); 2.675(0.5); 2.670(0.6); 2.666(0.5); 2.510(39.0);2.506(73.9); 2.501(95.5); 2.497(70.5); 2.493(35.5); 2.332(0.5);2.328(0.6); 2.324(0.5); 1.988(0.8); 1.957(0.6); 1.175(0.4); 0.000(1.1)18 1H-NMR(400.0 MHz, DMSO): δ = 8.540(2.0); 8.534(2.1); 8.501(1.4);8.498(1.5); 8.489(1.6); 8.486(1.6); 7.901(0.9); 7.897(1.0); 7.895(1.0);7.891(0.9); 7.881(1.0); 7.877(1.2); 7.874(1.2); 7.871(1.0); 7.520(2.5);7.485(1.3); 7.473(1.3); 7.465(1.2); 7.454(1.1); 7.453(1.2); 7.417(8.2);7.414(9.8); 6.366(3.4); 5.754(4.7); 4.355(0.3); 4.342(0.7); 4.329(0.4);3.831(16.0); 3.783(1.0); 3.456(0.6); 3.443(0.6); 3.439(0.7); 3.426(0.7);3.421(0.5); 3.409(15.4); 3.398(1.2); 3.318(21.5); 2.984(4.8);2.966(4.9); 2.944(0.7); 2.906(0.3); 2.888(0.3); 2.784(0.5); 2.524(0.7);2.511(13.1); 2.506(26.7); 2.502(35.6); 2.497(26.4); 2.493(13.3);1.988(0.6); 1.957(0.5); 1.175(0.3); 1.074(1.1); 1.056(2.3); 1.039(1.4);1.025(0.5); 1.019(0.5); 1.015(0.4); 1.007(0.9); 0.999(0.4); 0.995(0.5);0.987(0.6); 0.545(0.8); 0.534(2.2); 0.530(2.3); 0.525(1.1); 0.520(1.1);0.514(2.2); 0.510(2.1); 0.500(0.9); 0.277(0.9); 0.266(2.4); 0.263(2.5);0.255(2.2); 0.251(2.6); 0.240(0.7); 0.008(2.0); 0.000(53.3); −0.009(2.3)19 1H-NMR(400.0 MHz, CD₃CN): δ = 8.483(1.0); 8.480(1.1); 8.471(1.2);8.468(1.3); 8.463(1.6); 8.457(1.5); 7.738(0.8); 7.735(0.9); 7.732(0.8);7.728(0.7); 7.718(0.9); 7.714(1.0); 7.712(0.9); 7.708(0.8); 7.536(1.9);7.521(0.5); 7.517(0.7); 7.502(0.9); 7.498(1.5); 7.479(0.9); 7.460(1.8);7.442(1.1); 7.434(1.0); 7.430(1.5); 7.411(0.7); 7.407(1.2); 7.395(0.9);7.393(0.9); 7.386(0.8); 7.374(0.8); 6.372(2.8); 5.447(4.3); 4.479(6.7);3.823(15.5); 3.427(15.4); 3.348(16.0); 2.958(0.4); 2.191(38.7);1.972(0.5); 1.958(0.8); 1.952(4.2); 1.946(7.5); 1.940(10.1); 1.934(6.9);1.928(3.5); 0.008(0.4); 0.000(11.5); −0.009(0.4) 20 1H-NMR(400.0 MHz,CD₃CN): δ = 8.484(1.4); 8.480(1.6); 8.472(1.8); 8.468(1.8); 8.463(2.2);8.456(2.1); 7.738(0.8); 7.734(1.0); 7.731(1.0); 7.727(0.9); 7.717(1.0);7.714(1.1); 7.711(1.1); 7.707(1.0); 7.561(2.1); 7.510(0.5); 7.506(0.5);7.501(0.8); 7.498(1.0); 7.488(1.3); 7.483(1.1); 7.473(0.8); 7.454(2.4);7.453(2.6); 7.446(2.0); 7.441(2.7); 7.438(2.6); 7.405(1.1); 7.404(1.1);7.393(1.2); 7.392(1.2); 7.385(1.1); 7.383(1.1); 7.373(1.0); 7.371(1.0);6.371(3.5); 5.446(7.4); 5.438(0.8); 4.591(7.2); 3.877(0.9); 3.867(1.8);3.856(1.2); 3.848(1.3); 3.837(2.3); 3.823(16.0); 3.816(2.0); 3.631(0.6);3.619(0.7); 3.608(1.1); 3.598(0.8); 3.586(0.6); 3.576(0.3); 3.426(15.5);3.418(2.0); 3.407(1.5); 3.400(1.4); 3.382(1.5); 3.376(2.0); 3.353(1.1);3.346(1.2); 2.167(1.7); 2.155(0.8); 1.971(0.8); 1.963(0.9); 1.957(1.8);1.951(6.2); 1.945(10.9); 1.939(14.3); 1.933(11.0); 1.926(6.6);1.901(1.4); 1.897(1.3); 1.891(1.4); 1.568(0.6); 1.558(0.6); 1.544(1.0);1.535(1.4); 1.525(0.9); 1.521(0.9); 1.511(1.3); 1.501(0.9); 1.488(0.5);1.478(0.5); 0.008(2.6); 0.000(27.9); −0.009(3.6) 22 1H-NMR(400.0 MHz,CD₃CN): δ = 8.486(1.6); 8.482(1.6); 8.474(1.8); 8.470(2.1); 8.466(2.4);8.460(2.1); 8.127(1.6); 8.122(2.6); 8.119(1.6); 7.997(1.2); 7.994(0.9);7.977(1.4); 7.974(1.1); 7.943(1.3); 7.927(1.2); 7.924(1.5); 7.742(2.3);7.736(1.2); 7.732(1.1); 7.722(3.3); 7.712(1.0); 7.702(1.1); 7.405(1.2);7.394(1.2); 7.385(1.1); 7.373(1.0); 6.416(3.3); 5.446(12.4); 4.068(0.5);4.050(0.5); 3.869(16.0); 3.434(15.9); 3.091(15.8); 2.146(5.8);1.971(2.3); 1.963(0.9); 1.957(1.9); 1.952(6.6); 1.945(11.2);1.939(14.2); 1.933(10.0); 1.927(5.2); 1.221(0.5); 1.203(1.1);1.186(0.5); 0.000(30.3) 23 1H-NMR(400.0 MHz, CD₃CN): δ = 8.483(1.5);8.480(1.7); 8.471(1.7); 8.468(1.9); 8.460(2.2); 8.454(2.2); 7.740(0.9);7.736(1.0); 7.734(1.1); 7.730(0.9); 7.720(1.0); 7.716(1.1); 7.713(1.2);7.710(1.0); 7.406(1.2); 7.394(1.2); 7.386(1.1); 7.374(1.1); 7.357(3.0);7.259(6.6); 6.363(3.7); 5.447(1.1); 3.823(15.9); 3.542(1.0); 3.527(0.9);3.424(16.0); 2.957(0.7); 2.826(0.5); 2.483(15.1); 2.331(13.5);2.167(12.2); 1.971(1.1); 1.963(1.2); 1.957(2.5); 1.952(7.3);1.945(12.0); 1.939(15.1); 1.933(10.8); 1.927(5.7); 1.130(2.9);1.113(5.7); 1.095(2.8); 0.000(28.4) 24 1H-NMR(400.0 MHz, DMSO): δ =8.883(4.9); 8.692(1.4); 8.608(0.9); 8.564(0.4); 8.540(2.4); 8.487(1.8);8.477(2.1); 8.419(0.4); 8.413(0.4); 8.242(4.9); 8.065(2.2); 8.046(2.9);8.028(1.1); 8.015(2.0); 7.999(0.6); 7.971(0.8); 7.934(1.0); 7.917(4.7);7.914(4.7); 7.900(2.9); 7.897(3.1); 7.891(2.5); 7.888(2.4); 7.884(2.2);7.880(2.2); 7.874(2.6); 7.870(2.8); 7.864(2.4); 7.849(0.9); 7.845(0.9);7.825(1.3); 7.804(0.8); 7.797(0.7); 7.657(1.2); 7.652(1.2); 7.636(1.9);7.633(1.7); 7.623(1.5); 7.616(1.3); 7.609(1.0); 7.599(0.5); 7.591(0.5);7.580(0.4); 7.559(0.3); 7.475(1.4); 7.463(1.7); 7.454(1.7); 7.443(1.6);6.636(0.4); 6.352(3.4); 4.208(1.1); 4.056(0.6); 4.038(1.8); 4.021(1.9);4.003(0.8); 3.940(16.0); 3.799(0.3); 3.413(15.5); 3.365(0.6);3.321(16.8); 2.945(0.3); 2.671(0.6); 2.502(79.9); 2.498(64.9);2.329(0.5); 1.989(7.4); 1.958(0.5); 1.259(0.4); 1.235(2.4); 1.193(2.1);1.175(4.2); 1.158(2.2); 0.146(0.4); 0.000(86.1); −0.150(0.5) 251H-NMR(400.0 MHz, DMSO): δ = 8.638(2.7); 8.633(2.8); 8.535(2.1);8.529(2.2); 8.486(1.6); 8.476(1.6); 8.180(5.0); 7.890(0.9); 7.886(1.2);7.870(1.1); 7.866(1.4); 7.860(1.1); 7.856(0.9); 7.833(1.7); 7.813(0.9);7.536(0.4); 7.520(1.3); 7.515(1.7); 7.496(2.7); 7.489(1.8); 7.482(1.2);7.474(1.8); 7.462(1.6); 7.454(1.4); 7.442(1.3); 7.416(1.0); 7.410(1.0);7.395(1.3); 7.381(0.5); 7.374(0.6); 6.331(3.9); 5.754(0.8); 4.163(0.4);3.919(16.0); 3.418(0.9); 3.408(15.2); 3.365(0.4); 3.322(5.3);2.507(28.0); 2.502(36.5); 2.498(27.9); 1.235(0.7); 0.008(1.8);0.000(41.5) 26 1H-NMR(400.0 MHz, DMSO): δ = 8.936(5.1); 8.539(2.5);8.533(2.5); 8.488(1.6); 8.485(1.8); 8.476(1.7); 8.473(1.8); 8.127(5.1);7.939(3.2); 7.919(3.5); 7.893(0.9); 7.887(1.2); 7.883(1.0); 7.873(1.0);7.867(1.3); 7.863(1.0); 7.554(1.9); 7.535(3.3); 7.515(2.2); 7.474(1.4);7.462(1.4); 7.454(1.4); 7.442(1.3); 7.378(1.2); 7.360(2.0); 7.341(0.8);6.331(4.1); 4.203(0.4); 3.944(16.0); 3.422(0.6); 3.411(15.1);3.320(16.5); 2.944(1.0); 2.784(0.8); 2.532(0.4); 2.506(32.6);2.502(43.5); 2.497(33.2); 1.957(0.9); 1.901(1.0); 1.235(0.9);0.008(1.6); 0.000(41.6); −0.008 (2.0) 27 1H-NMR(400.0 MHz, CD3CN): δ =8.532(2.3); 8.528(3.2); 8.519(1.4); 8.516(1.4); 8.055(1.3); 8.034(1.4);7.995(1.2); 7.976(1.4); 7.789(0.7); 7.785(0.9); 7.782(0.8); 7.779(0.8);7.768(0.8); 7.764(1.0); 7.762(1.0); 7.758(0.9); 7.616(1.0); 7.598(1.7);7.578(2.0); 7.565(1.1); 7.562(1.3); 7.545(1.0); 7.541(1.2); 7.535(2.5);7.519(1.4); 7.515(1.9); 7.511(1.4); 7.497(0.7); 7.494(0.7); 7.450(2.3);7.440(1.2); 7.430(1.6); 7.419(1.0); 6.510(3.5); 4.068(0.7); 4.050(0.7);3.922(0.8); 3.551(16.0); 3.462(15.8); 3.446(0.9); 2.956(0.7);2.826(0.6); 2.155(12.8); 1.971(3.7); 1.964(0.8); 1.957(1.7); 1.951(8.8);1.945(16.1); 1.939(21.8); 1.933(15.6); 1.927(8.3); 1.221(0.8);1.203(1.6); 1.186(0.8); 0.008(1.8); 0.000(46.5) 28 1H-NMR(400.0 MHz,CD₃CN): δ = 8.689(2.3); 8.685(2.3); 8.537(2.2); 8.531(3.1); 8.522(1.5);8.519(1.4); 8.204(1.0); 8.199(1.0); 8.185(1.0); 8.181(1.1); 8.028(1.4);8.024(1.3); 8.006(1.5); 8.002(1.5); 7.787(0.8); 7.783(0.9); 7.781(0.9);7.777(0.8); 7.767(0.9); 7.763(1.0); 7.760(1.1); 7.757(0.9); 7.707(0.6);7.689(2.1); 7.671(3.5); 7.668(3.0); 7.656(0.7); 7.588(1.9); 7.566(1.7);7.452(1.1); 7.440(1.1); 7.431(1.0); 7.419(0.9); 6.519(3.4); 3.938(16.0);3.574(15.8); 3.464(15.8); 2.956(0.8); 2.825(0.7); 2.153(1.2);1.970(1.0); 1.964(0.4); 1.958(1.0); 1.952(5.1); 1.946(9.3); 1.940(12.6);1.933(8.8); 1.927(4.6); 0.008(1.1); 0.000(27.8); −0.008(1.4) 291H-NMR(400.0 MHz, CD₃CN): δ = 8.486(1.5); 8.483(1.5); 8.468(2.4);8.461(2.1); 7.751(0.8); 7.748(1.0); 7.745(1.0); 7.741(0.8); 7.731(1.0);7.727(1.1); 7.725(1.1); 7.721(0.9); 7.706(1.2); 7.701(1.2); 7.683(1.1);7.677(1.2); 7.479(0.6); 7.465(0.8); 7.458(1.6); 7.444(1.6); 7.435(1.1);7.429(1.0); 7.417(1.7); 7.415(1.7); 7.408(2.2); 7.399(1.2); 7.387(1.4);6.300(3.5); 5.446(0.7); 4.068(0.4); 4.050(0.5); 3.806(0.3); 3.717(0.6);3.665(0.7); 3.649(16.0); 3.556(15.5); 3.441(0.7); 3.426(15.7);3.320(0.6); 3.292(0.5); 2.957(0.7); 2.826(0.6); 2.140(4.1); 1.971(2.5);1.963(0.7); 1.951(8.1); 1.945(14.4); 1.939(19.0); 1.933(13.2);1.927(6.9); 1.270(0.8); 1.221(0.5); 1.204(1.0); 1.186(0.5); 0.000(40.2)30 1H-NMR(400.0 MHz, CD₃CN): δ = 8.530(3.1); 8.526(2.6); 8.524(2.5);8.518(1.7); 8.514(1.5); 8.192(1.3); 8.172(1.4); 7.784(0.8); 7.780(0.9);7.778(0.9); 7.774(0.8); 7.764(0.9); 7.760(1.1); 7.758(1.2); 7.754(1.0);7.674(0.6); 7.672(0.6); 7.655(1.3); 7.637(1.0); 7.634(0.9); 7.621(0.9);7.618(0.9); 7.600(1.4); 7.597(1.2); 7.583(0.7); 7.580(0.6); 7.530(1.1);7.517(1.2); 7.511(1.4); 7.497(1.6); 7.490(1.3); 7.469(1.0); 7.449(1.1);7.447(1.1); 7.435(1.1); 7.429(1.0); 7.427(1.0); 7.417(0.9); 7.415(1.0);7.341(1.3); 7.321(1.1); 7.315(1.4); 7.295(1.1); 6.503(3.4); 4.068(0.7);4.050(0.7); 3.553(16.0); 3.460(16.0); 3.447(0.4); 2.956(1.7);2.826(1.4); 2.138(7.5); 1.971(4.4); 1.964(0.7); 1.957(1.5); 1.952(7.5);1.945(13.6); 1.939(18.2); 1.933(12.7); 1.927(6.7); 1.221(0.8);1.204(1.6); 1.186(0.8); 0.008(1.6); 0.000(39.1); −0.008(2.0) 311H-NMR(400.0 MHz, CD₃CN): δ = 8.480(1.6); 8.471(1.6); 8.456(1.9);8.450(1.9); 8.011(2.3); 8.006(2.4); 7.731(2.1); 7.725(1.9); 7.710(2.7);7.705(2.4); 7.606(2.7); 7.585(1.9); 7.402(1.2); 7.390(1.2); 7.382(1.1);7.370(1.0); 6.391(3.4); 5.446(1.0); 4.387(1.3); 4.369(4.0); 4.351(4.0);4.333(1.4); 3.839(16.0); 3.563(0.6); 3.426(15.7); 2.957(3.3);2.826(2.9); 2.143(5.4); 1.971(3.2); 1.958(1.2); 1.952(5.9); 1.946(10.8);1.940(14.6); 1.933(10.2); 1.927(5.3); 1.378(0.5); 1.371(3.9);1.360(1.1); 1.353(7.8); 1.342(0.7); 1.336(3.9); 1.095(0.3); 0.008(1.2);0.000(31.4) 32 1H-NMR(400.0 MHz, CD₃CN): δ = 8.490(1.3); 8.486(1.4);8.474(3.1); 8.468(1.9); 7.978(1.2); 7.975(1.2); 7.959(1.3); 7.956(1.3);7.756(0.7); 7.752(0.8); 7.749(0.8); 7.745(0.7); 7.735(0.8); 7.731(0.9);7.729(1.0); 7.725(0.8); 7.688(0.4); 7.684(0.5); 7.669(1.3); 7.665(1.3);7.650(1.1); 7.646(1.0); 7.635(1.0); 7.631(1.2); 7.616(1.3); 7.612(1.4);7.597(0.5); 7.593(0.5); 7.435(1.4); 7.431(1.5); 7.421(1.2); 7.416(1.3);7.412(1.7); 7.401(1.0); 7.389(0.9); 6.310(3.3); 5.446(2.2); 3.877(0.4);3.638(16.0); 3.560(15.5); 3.429(15.5); 2.957(0.4); 1.971(1.3);1.963(0.6); 1.957(1.3); 1.951(7.2); 1.945(13.2); 1.939(17.7);1.933(12.3); 1.927(6.4); 1.203(0.5); 0.008(1.4); 0.000(37.4);−0.009(1.8) 33 1H-NMR(400.0 MHz, DMSO): δ = 8.697(3.4); 8.682(3.6);8.544(2.4); 8.538(2.5); 8.496(1.8); 8.486(1.9); 8.484(1.9); 7.980(0.4);7.974(0.6); 7.946(0.3); 7.934(0.4); 7.902(1.1); 7.897(0.9); 7.881(1.3);7.687(4.0); 7.672(4.0); 7.482(1.4); 7.471(1.5); 7.462(1.5); 7.450(1.4);6.458(3.0); 3.936(1.1); 3.915(16.0); 3.893(1.2); 3.418(15.7);3.404(2.4); 3.369(1.4); 3.330(2.4); 3.241(0.4); 2.756(2.1); 2.670(0.6);2.505(67.3); 2.501(87.1); 2.497(67.4); 2.328(0.6); 0.146(0.4);0.007(2.9); 0.000(72.0); −0.150(0.4) 35 1H-NMR(400.0 MHz, CD₃CN): δ =8.481(0.9); 8.203(2.1); 8.082(1.3); 8.062(1.4); 7.840(1.0); 7.821(1.2);7.737(0.9); 7.716(1.0); 7.614(1.2); 7.595(2.1); 7.575(1.0); 7.411(0.6);7.399(0.6); 7.392(0.6); 7.380(0.5); 6.403(1.0); 5.446(1.5); 4.380(1.3);4.362(4.0); 4.344(4.0); 4.327(1.4); 3.847(15.5); 3.433(16.0);2.151(2.0); 1.964(0.4); 1.958(1.1); 1.952(5.8); 1.946(10.5);1.939(14.0); 1.933(9.7); 1.927(5.0); 1.378(4.2); 1.361(8.3); 1.343(4.1);0.008(1.3); 0.000(30.0); −0.008(1.3) 36 1H-NMR(400.0 MHz, CD₃CN): δ =8.493(1.5); 8.485(2.8); 8.481(2.9); 8.121(2.3); 7.981(2.4); 7.971(1.1);7.961(3.1); 7.954(1.3); 7.945(0.9); 7.930(1.1); 7.759(0.8); 7.755(1.0);7.745(1.6); 7.741(1.7); 7.734(1.2); 7.728(1.1); 7.724(1.3); 7.720(1.2);7.598(0.4); 7.588(2.7); 7.581(1.5); 7.579(1.6); 7.574(1.5); 7.571(1.4);7.564(2.3); 7.418(1.1); 7.406(1.1); 7.398(1.0); 7.386(1.0); 6.429(3.0);4.068(0.5); 4.050(0.5); 3.921(15.6); 3.445(16.0); 2.158(0.9);1.971(2.3); 1.963(0.4); 1.957(0.8); 1.951(4.3); 1.945(7.8); 1.939(10.4);1.933(7.2); 1.927(3.7); 1.221(0.6); 1.203(1.2); 1.185(0.6); 0.008(0.8);0.000(17.5); −0.008(0.7) 37 1H-NMR(400.0 MHz, CD₃CN): δ = 8.479(1.6);8.476(1.7); 8.467(1.8); 8.464(1.8); 8.456(2.1); 8.450(2.1); 8.415(0.4);8.409(0.4); 7.908(2.3); 7.903(2.5); 7.747(1.3); 7.741(1.2); 7.725(2.4);7.719(2.1); 7.708(1.0); 7.705(1.1); 7.702(1.1); 7.699(0.9); 7.399(1.3);7.388(1.4); 7.379(1.1); 7.368(1.2); 7.186(2.2); 7.164(2.1); 6.348(3.5);6.164(0.4); 5.446(4.8); 3.898(13.8); 3.822(16.0); 3.816(15.6);3.806(2.9); 3.422(14.2); 3.385(2.7); 2.143(5.2); 1.971(1.3); 1.963(0.6);1.952(6.0); 1.945(10.6); 1.939(13.9); 1.933(9.8); 1.927(5.1);1.221(0.3); 1.203(0.6); 0.000(22.4) 39 1H-NMR(400.0 MHz, DMSO): δ =8.527(2.2); 8.521(2.3); 8.485(1.5); 8.482(1.6); 8.473(1.6); 8.470(1.6);8.183(4.5); 7.962(1.7); 7.959(1.8); 7.955(2.0); 7.952(1.8); 7.886(0.8);7.882(1.0); 7.880(1.0); 7.876(0.9); 7.866(0.9); 7.862(1.1); 7.859(1.1);7.856(0.9); 7.683(1.5); 7.676(1.6); 7.670(1.8); 7.663(1.6); 7.471(1.3);7.457(2.6); 7.454(2.3); 7.444(1.8); 7.441(2.3); 6.324(3.6); 3.891(16.0);3.403(15.2); 2.891(0.6); 2.732(0.5); 2.528(0.9); 2.524(1.0);2.510(18.2); 2.506(36.5); 2.502(48.2); 2.497(35.9); 0.008(1.8);0.000(47.1) 40 1H-NMR(400.0 MHz, CD₃CN): δ = 8.479(1.3); 8.476(1.4);8.467(1.4); 8.464(1.5); 8.452(2.0); 8.446(2.0); 7.732(0.7); 7.728(0.9);7.726(0.9); 7.722(0.8); 7.711(0.8); 7.707(1.0); 7.705(1.0); 7.701(0.9);7.401(1.2); 7.389(1.2); 7.380(1.1); 7.368(1.0); 7.275(1.5); 7.256(1.9);7.115(1.4); 7.112(1.6); 7.096(1.1); 7.093(1.2); 6.980(2.6); 6.978(2.5);6.343(3.6); 4.721(9.6); 4.215(1.3); 4.197(3.8); 4.179(3.8); 4.162(1.3);3.794(16.0); 3.418(15.8); 2.956(0.4); 2.283(11.7); 2.150(2.2);1.971(1.6); 1.963(0.5); 1.957(1.3); 1.951(7.1); 1.945(12.9);1.939(17.4); 1.933(12.0); 1.926(6.2); 1.269(0.5); 1.245(4.3);1.228(8.5); 1.210(4.2); 1.203(0.8); 1.185(0.3); 0.008(2.1); 0.000(53.1);−0.008(2.3) 41 1H-NMR(400.0 MHz, CD₃CN): δ = 8.483(1.4); 8.480(1.4);8.471(1.5); 8.468(1.4); 8.459(2.0); 8.453(1.9); 7.735(0.8); 7.731(0.9);7.729(0.9); 7.725(0.8); 7.715(0.9); 7.711(1.0); 7.709(1.0); 7.705(0.8);7.417(1.1); 7.404(1.2); 7.396(2.3); 7.384(1.1); 7.376(1.6); 7.373(1.1);7.208(1.5); 7.189(1.3); 7.102(1.4); 7.096(1.9); 7.093(1.5); 7.021(1.1);7.020(1.1); 7.015(1.0); 7.001(1.0); 6.999(1.0); 6.994(0.9); 6.363(3.5);5.447(8.7); 4.703(9.4); 4.227(1.3); 4.209(3.8); 4.191(3.8); 4.174(1.3);4.068(0.5); 4.050(0.5); 3.814(15.9); 3.423(16.0); 2.175(10.6);1.971(2.2); 1.963(0.5); 1.957(1.2); 1.951(5.9); 1.945(10.6);1.939(14.1); 1.933(9.7); 1.927(5.0); 1.256(4.4); 1.238(8.5); 1.221(4.7);1.203(1.1); 1.185(0.5); 0.008(3.1); 0.000(61.5); −0.009(3.1);−0.150(0.3) 42 1H-NMR(400.0 MHz, CD₃CN): δ = 8.480(1.5); 8.477(1.5);8.468(1.6); 8.465(1.5); 8.445(2.2); 8.439(2.2); 7.731(0.8); 7.727(1.1);7.725(1.0); 7.721(0.8); 7.710(1.0); 7.707(1.2); 7.704(1.1); 7.701(0.9);7.401(1.3); 7.390(1.3); 7.381(1.2); 7.369(1.1); 7.159(0.7); 7.154(0.7);7.142(0.7); 7.137(0.8); 7.132(0.8); 7.127(0.8); 7.115(0.7); 7.110(0.7);7.042(1.4); 7.024(1.4); 6.350(3.6); 4.798(9.8); 4.231(1.3); 4.213(3.9);4.196(4.0); 4.178(1.3); 4.068(0.9); 4.050(0.9); 3.800(16.0);3.418(15.9); 2.957(0.4); 2.826(0.4); 2.143(6.8); 1.971(4.2); 1.957(1.2);1.951(5.3); 1.945(9.4); 1.939(12.5); 1.933(8.8); 1.927(4.6); 1.253(4.3);1.235(8.5); 1.217(4.3); 1.203(2.0); 1.185(1.0); 0.007(2.6); 0.000(47.7)43 1H-NMR(400.0 MHz, CD₃CN): δ = 8.480(1.5); 8.478(1.6); 8.469(1.5);8.466(1.6); 8.451(2.2); 8.445(2.2); 7.733(0.8); 7.729(1.0); 7.727(1.0);7.724(0.8); 7.713(0.9); 7.709(1.1); 7.707(1.1); 7.402(1.2); 7.390(1.2);7.382(1.1); 7.370(1.0); 7.270(0.9); 7.249(1.6); 7.242(0.8); 7.221(1.6);7.214(1.3); 7.209(1.7); 7.198(1.3); 7.193(1.7); 7.187(2.5); 7.178(0.7);7.173(0.5); 7.166(0.6); 7.161(0.4); 6.345(3.8); 5.447(4.4); 4.769(9.5);4.226(1.3); 4.208(3.9); 4.190(3.9); 4.172(1.3); 4.085(0.5); 4.068(1.5);4.050(1.5); 4.032(0.5); 3.790(15.8); 3.419(16.0); 2.956(0.8);2.825(0.7); 2.171(13.4); 1.971(6.8); 1.957(1.0); 1.952(4.5); 1.946(8.1);1.939(10.7); 1.933(7.5); 1.927(3.9); 1.249(4.3); 1.231(8.4); 1.221(1.9);1.214(4.2); 1.203(3.3); 1.185(1.6); 0.008(2.0); 0.000(41.7) 441H-NMR(400.0 MHz, CD₃CN): δ = 8.484(1.4); 8.481(1.4); 8.472(1.5);8.469(1.5); 8.461(2.0); 8.455(2.0); 8.115(1.2); 8.109(1.3); 8.097(1.3);8.092(1.2); 7.829(0.7); 7.823(0.7); 7.818(0.8); 7.812(0.8); 7.808(0.8);7.802(0.8); 7.796(0.8); 7.791(0.7); 7.735(0.8); 7.731(1.0); 7.729(1.0);7.725(0.8); 7.715(1.0); 7.711(1.1); 7.708(1.1); 7.705(0.9); 7.403(1.2);7.392(1.2); 7.383(1.1); 7.371(1.0); 7.337(1.3); 7.315(1.4); 7.310(1.4);7.288(1.2); 6.380(3.6); 5.446(2.4); 4.383(1.3); 4.365(4.0); 4.347(4.0);4.329(1.4); 3.827(15.5); 3.428(16.0); 2.957(8.5); 2.826(7.3);2.159(10.2); 1.971(8.6); 1.957(1.2); 1.951(5.4); 1.945(9.6);1.939(12.7); 1.933(8.7); 1.927(4.5); 1.368(4.1); 1.350(8.1); 1.332(4.0);1.203(0.4); 0.000(11.1) 45 1H-NMR(400.0 MHz, CD₃CN): δ = 8.474(0.7);7.738(0.5); 7.735(0.6); 7.729(0.5); 7.718(0.6); 7.714(0.7); 7.709(0.5);7.588(1.5); 7.562(0.6); 7.544(1.0); 7.503(0.5); 7.484(1.3); 7.465(1.7);7.462(1.4); 7.443(0.3); 7.406(0.6); 7.394(0.6); 7.386(0.6); 7.374(0.5);6.384(1.3); 5.447(1.5); 5.142(5.1); 3.867(0.5); 3.827(10.0);3.428(10.1); 2.956(16.0); 2.826(13.7); 2.183(3.7); 1.970(15.0);1.957(0.7); 1.951(2.7); 1.945(4.8); 1.939(6.3); 1.932(4.4); 1.926(2.3);1.674(0.4); 1.667(0.4); 1.655(0.8); 1.643(0.4); 1.636(0.4); 0.915(0.7);0.908(2.2); 0.904(1.8); 0.895(3.3); 0.887(0.9); 0.879(1.0); 0.874(1.9);0.867(0.7); 0.000(5.8) 46 1H-NMR(400.0 MHz, CD₃CN): δ = 8.460(1.8);7.732(1.2); 7.730(1.1); 7.726(0.9); 7.715(1.1); 7.711(1.3); 7.709(1.3);7.550(1.3); 7.532(1.3); 7.519(0.8); 7.514(0.7); 7.506(0.9); 7.499(1.1);7.493(0.8); 7.485(0.9); 7.402(1.0); 7.390(1.2); 7.382(1.1); 7.370(1.0);7.202(1.3); 7.180(1.6); 7.178(1.7); 7.156(1.2); 7.100(0.7); 6.359(2.0);5.447(4.0); 4.425(3.6); 4.410(3.6); 3.794(16.0); 3.422(16.0);3.384(1.7); 2.955(8.1); 2.824(7.1); 2.179(11.6); 1.970(7.8); 1.957(1.2);1.952(4.2); 1.946(7.4); 1.940(9.5); 1.933(6.7); 1.927(3.4); 1.531(0.3);1.520(0.7); 1.512(0.8); 1.500(1.3); 1.488(0.9); 1.481(0.8); 1.469(0.4);1.269(0.4); 0.770(0.7); 0.758(2.0); 0.751(2.9); 0.747(2.5); 0.740(2.8);0.733(1.2); 0.724(0.5); 0.710(1.4); 0.703(2.7); 0.696(1.7); 0.690(1.5);0.683(2.8); 0.676(1.4); 0.668(0.6); 0.665(0.6); 0.000(4.1) 471H-NMR(400.0 MHz, DMSO): δ = 8.663(1.4); 8.653(1.4); 8.531(2.2);8.525(2.3); 8.475(1.8); 8.471(2.0); 8.463(2.1); 8.460(2.3); 8.433(6.4);8.317(0.9); 7.979(1.3); 7.959(2.2); 7.917(1.0); 7.913(1.1); 7.898(1.4);7.894(1.5); 7.887(0.9); 7.879(1.5); 7.866(0.9); 7.863(1.1); 7.860(1.1);7.856(0.9); 7.463(1.2); 7.450(1.2); 7.442(2.0); 7.430(1.9); 7.423(1.1);7.420(1.0); 7.411(0.8); 7.408(0.9); 6.462(3.0); 4.172(16.0); 4.015(0.4);3.993(0.5); 3.979(0.4); 3.936(0.7); 3.916(0.5); 3.893(0.6); 3.864(0.7);3.552(7.4); 3.420(17.4); 3.242(0.7); 3.121(0.4); 3.105(0.3); 2.675(1.3);2.671(1.8); 2.667(1.4); 2.541(0.9); 2.506(206.9); 2.502(276.0);2.498(215.5); 2.333(1.3); 2.329(1.8); 2.324(1.4); 0.008(1.0);0.000(32.4) 48 1H-NMR(400.0 MHz, CD₃CN): δ = 8.484(1.7); 8.471(2.0);8.465(2.5); 8.459(2.3); 7.767(3.8); 7.746(1.7); 7.741(1.6); 7.716(1.3);7.660(0.7); 7.641(2.0); 7.628(1.8); 7.609(1.6); 7.590(0.5); 7.407(1.2);7.395(1.3); 7.387(1.2); 7.375(1.1); 6.983(1.2); 6.843(2.3); 6.703(1.2);6.398(3.6); 3.844(15.8); 3.431(16.0); 2.151(4.4); 1.963(2.1);1.951(8.9); 1.945(15.9); 1.939(21.2); 1.933(15.2); 1.927(8.0);1.842(0.4); 1.270(0.3); 0.000(58.7) 49 1H-NMR(600.1 MHz, CD₃CN): δ =8.486(1.1); 8.484(1.1); 8.478(1.2); 8.476(1.2); 8.470(1.4); 8.466(1.5);8.044(1.4); 8.037(1.6); 7.971(0.7); 7.969(0.9); 7.968(0.9); 7.966(0.7);7.958(0.8); 7.956(1.1); 7.955(1.0); 7.953(0.8); 7.923(0.7); 7.909(0.8);7.796(1.1); 7.783(1.9); 7.770(0.8); 7.747(0.6); 7.745(0.7); 7.743(0.7);7.741(0.6); 7.734(0.7); 7.731(0.8); 7.730(0.8); 7.727(0.7); 7.409(0.8);7.408(0.8); 7.401(0.8); 7.400(0.8); 7.395(0.8); 7.394(0.7); 7.387(0.7);7.386(0.7); 6.437(1.7); 3.858(16.0); 3.436(15.6); 3.275(0.3);1.956(0.7); 1.951(0.8); 1.948(4.4); 1.944(7.8); 1.939(11.4); 1.935(7.7);1.931(3.9); 1.135(1.4); 0.000(1.9) 50 1H-NMR(400.0 MHz, CD₃CN): δ =8.486(1.3); 8.482(1.3); 8.474(1.4); 8.470(1.4); 8.462(1.8); 8.455(1.7);7.903(1.2); 7.887(1.9); 7.879(0.7); 7.873(0.5); 7.866(0.6); 7.861(0.4);7.742(0.7); 7.738(0.8); 7.736(0.8); 7.732(0.7); 7.722(0.8); 7.718(0.9);7.715(0.9); 7.712(0.8); 7.453(0.8); 7.432(0.9); 7.406(1.7); 7.394(1.1);7.393(1.0); 7.386(1.0); 7.374(0.9); 6.391(2.9); 5.447(6.5); 3.827(15.5);3.763(0.4); 3.428(16.0); 3.388(0.4); 2.167(8.3); 1.958(0.7); 1.952(3.7);1.946(6.7); 1.940(9.1); 1.934(6.2); 1.928(3.2); 0.008(1.1); 0.000(24.6);−0.009(0.9) 51 1H-NMR(400.0 MHz, CD₃CN): δ = 8.485(1.4); 8.482(1.4);8.473(1.5); 8.470(1.5); 8.455(2.0); 8.449(2.0); 7.881(2.1); 7.842(2.2);7.808(2.0); 7.738(0.8); 7.734(1.0); 7.731(0.9); 7.727(0.8); 7.717(0.9);7.713(1.0); 7.711(1.0); 7.707(0.8); 7.406(1.2); 7.394(1.2); 7.385(1.1);7.374(1.0); 6.412(3.0); 5.447(4.9); 3.898(0.6); 3.860(16.0); 3.441(0.7);3.430(15.9); 2.156(22.2); 1.964(0.5); 1.958(1.0); 1.952(6.0);1.946(10.9); 1.940(14.8); 1.933(10.1); 1.927(5.2); 0.008(1.5);0.000(37.5); −0.009(1.6) 52 1H-NMR(400.0 MHz, DMSO): δ = 8.559(1.0);8.514(0.8); 8.364(0.5); 7.988(1.3); 7.965(2.6); 7.904(1.0); 7.884(1.1);7.857(1.0); 7.837(1.5); 7.761(1.2); 7.742(1.8); 7.722(0.7); 7.494(0.8);7.483(0.8); 7.474(0.8); 7.462(0.7); 6.422(3.1); 3.903 (6.1);3.875(16.0); 3.419(14.8); 3.331(95.2); 2.676(0.4); 2.672(0.6);2.667(0.4); 2.525(1.5); 2.507 (70.9); 2.503(99.3); 2.498(76.3);2.334(0.4); 2.329(0.5); 2.325(0.4); 1.236(0.4); 0.000(4.5) 531H-NMR(400.0 MHz, CD₃CN): δ = 8.488(1.4); 8.484(1.4); 8.476(1.5);8.472(1.4); 8.462(2.0); 8.455(2.0); 8.164(4.5); 8.078(1.9); 7.746(0.8);7.742(0.9); 7.740(0.9); 7.736(0.7); 7.726(0.9); 7.722(1.0); 7.719(1.0);7.716(0.8); 7.410(1.1); 7.398(1.1); 7.390(1.0); 7.378(1.0); 6.438(3.0);5.447(7.6); 3.880(16.0); 3.437(15.7); 2.170(23.1); 1.958(0.7);1.953(4.1); 1.947(7.4); 1.940(10.0); 1.934(6.8); 1.928(3.5); 0.008(0.8);0.000(19.4); −0.009(0.7) 54 1H-NMR(400.0 MHz, CD₃CN): δ = 8.485(1.5);8.481(1.4); 8.473(1.5); 8.469(1.5); 8.457(2.0); 8.451(2.0); 7.757(2.3);7.742(0.9); 7.738(1.0); 7.735(0.9); 7.732(0.8); 7.721(0.9); 7.718(1.1);7.715(1.0); 7.711(0.8); 7.653(1.0); 7.629(0.9); 7.566(0.9); 7.544(1.0);7.407(1.1); 7.395(1.1); 7.387(1.0); 7.375(1.0); 6.415(3.1); 3.868(16.0);3.431(15.9); 2.188(24.5); 1.959(0.5); 1.953(2.6); 1.947(4.8);1.941(6.4); 1.935(4.4); 1.928(2.2); 0.000(7.3) 55 1H-NMR(400.0 MHz,CD3CN): δ = 8.483(1.3); 8.480(1.4); 8.471(1.4); 8.468(1.4); 8.453(1.8);8.447(1.8); 8.126(2.6); 8.067(0.6); 8.046(3.3); 8.040(2.6); 8.037(2.3);8.019(0.4); 8.016(0.4); 7.740(0.8); 7.736(1.0); 7.734(0.9); 7.730(0.8);7.720(0.9); 7.716(1.1); 7.713(1.1); 7.710(0.9); 7.404(1.1); 7.392(1.1);7.383(1.0); 7.372(1.0); 6.458(2.8); 5.447(0.3); 3.891(16.0);3.434(15.8); 2.166(22.0); 1.958(0.7); 1.952(3.9); 1.946(7.2);1.940(9.7); 1.934(6.7); 1.928(3.4); 0.008(1.0); 0.000(22.3); −0.008(1.0)56 1H-NMR(400.0 MHz, CD₃CN): δ = 8.484(1.0); 8.470(1.2); 8.462(1.4);8.021(0.4); 7.741(0.7); 7.738(0.9); 7.735(0.8); 7.731(0.7); 7.721(0.8);7.717(1.0); 7.715(1.0); 7.711(0.8); 7.597(1.0); 7.581(3.3); 7.516(0.9);7.497(1.8); 7.477(1.2); 7.456(1.4); 7.437(0.7); 7.408(0.9); 7.396(0.9);7.388(0.9); 7.376(0.8); 6.382(2.5); 5.446(1.7); 3.826(16.0); 3.613(0.9);3.585(2.7); 3.557(2.7); 3.528(0.9); 3.429(16.0); 2.151(1.8); 2.106(0.7);1.963(0.8); 1.957(1.8); 1.951(10.1); 1.945(18.3); 1.939(24.7);1.933(16.8); 1.926(8.6); 1.270(0.3); 0.146(0.3); 0.008(2.9);0.000(68.2); −0.009(2.5); −0.150(0.3) 57 1H-NMR(400.0 MHz, CD₃CN): δ =8.484(0.9); 8.470(1.4); 8.030(0.7); 7.894(1.0); 7.872(2.9); 7.764(0.7);7.745(2.2); 7.728(0.8); 7.725(1.0); 7.722(1.0); 7.718(1.3); 7.716(1.3);7.696(1.3); 7.677(0.5); 7.412(0.8); 7.400(0.8); 7.392(0.8); 7.380(0.7);6.411(2.4); 5.447(1.7); 3.839(16.0); 3.433(15.9); 2.959(1.3);2.829(1.0); 2.190(0.4); 1.974(1.2); 1.964(0.5); 1.958(1.1); 1.952(5.8);1.946(10.6); 1.940(14.3); 1.933(9.8); 1.927(5.0); 0.008(1.8);0.000(40.7); −0.009(1.5) 58 1H-NMR(400.0 MHz, CD₃CN): δ = 8.486(1.0);8.475(1.1); 8.461(1.3); 7.958(2.3); 7.954(1.6); 7.907(0.9); 7.904(1.2);7.900(0.8); 7.887(1.0); 7.884(1.4); 7.880(0.9); 7.816(0.8); 7.813(1.2);7.809(0.8); 7.796(1.1); 7.793(1.5); 7.790(0.9); 7.745(0.7); 7.742(0.9);7.739(0.8); 7.736(0.7); 7.725(0.8); 7.721(1.0); 7.719(0.9); 7.715(0.7);7.656(1.3); 7.636(2.2); 7.617(0.9); 7.411(0.8); 7.399(0.8); 7.391(0.8);7.379(0.7); 6.410(2.9); 5.448(2.1); 3.841(15.8); 3.430(16.0);2.205(14.1); 1.959(0.7); 1.953(3.8); 1.947(7.0); 1.940(9.5); 1.934(6.5);1.928(3.4); 0.008(0.4); 0.000(10.4); −0.009(0.4) 59 1H-NMR(400.0 MHz,CD₃CN): δ = 8.482(1.6); 8.479(1.5); 8.471(1.7); 8.467(1.5); 8.450(2.1);8.444(2.2); 8.018(2.5); 8.013(2.8); 7.876(1.4); 7.870(1.3); 7.854(1.7);7.849(1.7); 7.736(0.9); 7.733(1.1); 7.730(1.0); 7.726(0.8); 7.716(1.1);7.707(3.6); 7.685(2.1); 7.404(1.2); 7.392(1.2); 7.383(1.1); 7.371(1.0);6.399(3.2); 3.838(16.0); 3.425(16.0); 2.152(11.4); 1.964(0.4);1.958(1.1); 1.952(4.8); 1.946(8.6); 1.940(11.2); 1.934(7.9); 1.927(4.1);0.000(11.5) 60 1H-NMR(400.0 MHz, DMSO): δ = 8.536(2.4); 8.530(2.5);8.500(1.7); 8.497(1.8); 8.488(1.8); 8.485(1.7); 8.003(3.5); 8.000(2.4);7.996(1.3); 7.989(1.2); 7.974(1.0); 7.971(1.0); 7.968(1.1); 7.914(1.0);7.910(1.1); 7.902(1.2); 7.897(1.2); 7.895(1.2); 7.891(1.5); 7.885(1.3);7.881(1.7); 7.871(1.0); 7.482(1.3); 7.470(1.3); 7.462(1.3); 7.450(1.2);6.440(2.9); 5.755(0.5); 3.893(16.0); 3.414(15.1); 3.325(93.2);2.671(0.3); 2.510(21.8); 2.506(42.8); 2.502(55.6); 2.497(40.8);2.329(0.3); 0.000(1.5) 61 1H-NMR(400.0 MHz, CD₃CN): δ = 8.517(1.8);8.514(1.6); 8.505(1.8); 8.485(2.6); 8.479(2.3); 8.238(2.9); 8.201(2.7);8.178(2.6); 7.778(1.0); 7.773(1.2); 7.758(1.1); 7.752(1.3); 7.442(1.3);7.430(1.4); 7.422(1.2); 7.410(1.1); 6.469(3.2); 5.481(0.5); 5.477(1.3);3.900(16.0); 3.468(6.3); 3.464(15.9); 2.242(103.2); 2.201(0.9);1.994(1.1); 1.987(3.5); 1.982(9.2); 1.976(14.9); 1.971(18.5);1.965(12.7); 1.959(6.5) 62 1H-NMR(400.0 MHz, CD₃CN): δ = 8.498(1.3);8.495(1.3); 8.486(1.4); 8.483(1.4); 8.459(1.7); 8.452(1.8); 7.855(1.2);7.850(1.3); 7.833(1.4); 7.828(1.5); 7.734(0.7); 7.730(0.8); 7.727(0.8);7.724(0.7); 7.714(0.8); 7.710(0.9); 7.707(0.9); 7.703(0.8); 7.641(2.5);7.636(2.4); 7.418(1.0); 7.406(1.0); 7.404(0.9); 7.397(0.9); 7.385(0.9);7.384(0.9); 7.230(2.2); 7.208(2.0); 6.381(3.0); 6.222(0.4); 5.446(0.5);3.883(14.3); 3.763(2.6); 3.564(16.0); 3.422(15.9); 3.387(2.8);2.764(0.6); 2.751(0.6); 2.144(31.5); 1.963(0.6); 1.957(1.2); 1.951(7.8);1.945(14.5); 1.939(19.9); 1.933(13.8); 1.927(7.2); 0.008(0.4);0.000(12.7); −0.009(0.5) 63 1H-NMR(400.0 MHz, CD₃CN): δ = 8.484(1.1);8.481(1.2); 8.472(1.2); 8.469(1.2); 8.452(1.4); 8.446(1.5); 7.982(0.9);7.976(1.2); 7.967(1.0); 7.961(1.2); 7.942(0.8); 7.936(0.6); 7.929(0.8);7.923(0.6); 7.920(0.9); 7.914(0.7); 7.907(0.8); 7.901(0.7); 7.739(0.7);7.735(0.8); 7.732(0.8); 7.728(0.7); 7.718(0.8); 7.714(0.9); 7.712(0.9);7.708(0.8); 7.453(1.1); 7.430(2.0); 7.407(1.5); 7.405(1.0); 7.394(0.9);7.393(0.9); 7.386(0.9); 7.384(0.8); 7.374(0.8); 7.372(0.8); 6.384(2.6);3.822(16.0); 3.425(16.0); 2.178(1.0); 1.964(0.4); 1.958(0.8);1.952(4.4); 1.946(8.1); 1.940(11.1); 1.933(7.7); 1.927(4.0); 0.000(3.2)64 1H-NMR(400.0 MHz, CD₃CN): δ = 9.035(2.4); 9.030(2.4); 8.931(2.5);8.926(2.4); 8.488(1.4); 8.484(1.3); 8.476(1.5); 8.472(1.4); 8.456(1.9);8.450(1.9); 8.330(1.6); 8.325(2.9); 8.320(1.5); 7.748(0.8); 7.744(0.9);7.742(0.9); 7.738(0.7); 7.728(0.9); 7.724(1.0); 7.721(1.0); 7.717(0.8);7.411(1.1); 7.399(1.1); 7.390(1.0); 7.378(1.0); 6.446(2.7); 3.871(16.0);3.763(0.8); 3.433(15.7); 3.387(0.9); 2.207(0.7); 1.964(0.5); 1.958(1.0);1.952(4.7); 1.946(8.5); 1.940(11.5); 1.934(7.9); 1.928(3.9); 0.008(0.3);0.000(7.4) 65 1H-NMR(400.0 MHz, CD₃CN): δ = 8.494(1.8); 8.488(1.7);8.479(1.3); 8.467(1.2); 8.444(1.6); 8.017(1.1); 8.013(1.9); 8.007(1.6);7.728(0.8); 7.708(0.9); 7.403(0.7); 7.391(0.8); 7.382(0.7); 7.370(0.6);6.346(2.0); 5.451(1.3); 5.447(1.9); 3.808(5.6); 3.804(7.9); 3.420(5.6);3.416(7.8); 3.307(11.3); 3.303(16.0); 2.197(1.1); 1.956(3.4);1.950(6.6); 1.945(9.2); 1.944(9.3); 1.939(10.6); 1.933(7.5); 0.004(1.7);0.000(2.4) 66 1H-NMR(400.0 MHz, CD₃CN): δ = 8.565(1.6); 8.559(1.6);8.480(1.0); 8.477(1.0); 8.468(1.1); 8.465(0.9); 8.446(1.4); 8.440(1.5);8.096(1.7); 8.090(1.7); 7.734(0.6); 7.731(0.7); 7.728(0.7); 7.714(0.7);7.710(0.8); 7.708(0.7); 7.404(0.7); 7.392(0.7); 7.384(0.7); 7.372(0.6);6.363(2.1); 5.446(3.7); 3.817(8.5); 3.762(16.0); 3.419(8.4);2.145(27.4); 2.143(28.0); 1.963(1.6); 1.951(15.1); 1.945(26.4);1.939(34.0); 1.933(24.5); 1.929(12.7); 1.927(12.6); 1.135(0.9);0.000(7.9) 67 1H-NMR(400.0 MHz, CD₃CN): δ = 8.576(4.2); 8.483(2.6);8.480(2.5); 8.472(2.8); 8.450(4.0); 8.230(4.4); 8.039(1.4); 7.737(1.9);7.720(2.1); 7.716(2.1); 7.407(1.6); 7.395(2.0); 7.388(1.7); 7.376(1.4);6.385(4.2); 5.448(8.4); 4.560(1.5); 4.543(4.2); 4.525(4.2); 4.508(1.5);3.820(16.0); 3.423(15.9); 2.467(0.4); 2.188(4.9); 1.951(17.0);1.946(25.2); 1.940(26.9); 1.934(19.6); 1.438(4.5); 1.420(8.4);1.403(4.3); 1.203(0.4); 1.134(0.6); 0.000(4.5) 68 1H-NMR(400.0 MHz,CD₃CN): δ = 8.602(2.6); 8.596(2.7); 8.484(1.4); 8.481(1.5); 8.473(1.5);8.469(1.5); 8.450(2.1); 8.444(2.0); 8.240(2.9); 8.234(2.8); 8.048(0.9);7.742(0.8); 7.738(0.9); 7.736(0.9); 7.732(0.8); 7.722(0.9); 7.718(1.0);7.715(1.0); 7.712(0.9); 7.407(1.1); 7.395(1.1); 7.387(1.1); 7.375(1.0);6.387(3.0); 5.447(2.7); 4.077(16.0); 3.820(15.6); 3.424(15.3);2.252(0.7); 2.208(0.6); 2.171(0.4); 2.114(0.3); 2.107(0.3); 1.964(0.9);1.958(1.8); 1.952(7.6); 1.946(13.4); 1.940(17.8); 1.934(12.4);1.927(6.3); 0.000(1.9) 69 1H-NMR(400.0 MHz, CD₃CN): δ = 8.486(0.9);8.474(0.9); 8.450(1.1); 8.444(1.1); 7.916(0.9); 7.912(2.3); 7.907(3.8);7.903(3.2); 7.899(1.0); 7.854(1.7); 7.850(2.2); 7.846(1.3); 7.738(0.7);7.734(0.8); 7.731(0.8); 7.728(0.7); 7.717(0.8); 7.714(0.9); 7.711(0.8);7.707(0.8); 7.406(0.9); 7.394(0.9); 7.386(0.8); 7.374(0.8); 6.411(2.4);5.447(0.3); 3.852(16.0); 3.427(15.9); 3.388(1.2); 3.303(1.3);2.464(0.4); 2.162(60.6); 2.119(0.4); 2.113(0.5); 2.107(0.5); 2.101(0.4);1.964(2.2); 1.958(4.1); 1.952(26.6); 1.946(49.4); 1.939(68.6);1.933(47.5); 1.927(24.2); 1.914(0.3); 1.768(0.4); 0.000(0.6) 701H-NMR(400.0 MHz, DMSO): δ = 8.551(2.0); 8.545(2.1); 8.491(1.5);8.488(1.5); 8.479(1.5); 8.476(1.4); 8.313(0.4); 7.903(0.9); 7.900(1.0);7.897(1.0); 7.893(0.9); 7.883(1.0); 7.879(1.1); 7.876(1.1); 7.873(0.9);7.737(1.5); 7.718(1.6); 7.674(1.5); 7.653(1.8); 7.476(1.2); 7.463(1.2);7.455(1.2); 7.443(1.1); 7.419(1.0); 7.414(4.3); 7.412(4.0); 7.401(1.4);7.398(1.6); 7.380(1.1); 7.377(1.0); 7.338(1.3); 7.336(1.2); 7.319(1.7);7.300(0.8); 7.298(0.7); 6.478(2.9); 5.753(0.4); 4.067(16.0);3.427(14.9); 3.319(168.6); 2.676(0.6); 2.671(0.7); 2.666(0.6);2.524(1.8); 2.511(43.7); 2.506(91.4); 2.502(126.3); 2.497(92.5);2.493(43.2); 2.333(0.5); 2.329(0.7); 2.324(0.5); 1.988(0.5); 0.146(0.4);0.008(2.9); 0.000(93.6); −0.009(3.0); −0.149(0.4) 71 1H-NMR(400.0 MHz,DMSO): δ = 8.556(2.2); 8.550(2.3); 8.496(1.7); 8.492(1.7); 8.484(1.8);8.480(1.7); 7.984(1.8); 7.974(2.1); 7.965(2.4); 7.960(2.1); 7.906(0.9);7.902(1.0); 7.899(1.0); 7.896(0.9); 7.886(1.0); 7.882(1.1); 7.879(1.1);7.875(1.0); 7.597(6.6); 7.565(0.8); 7.556(2.8); 7.553(2.7); 7.545(4.4);7.539(4.6); 7.530(0.5); 7.475(1.3); 7.463(1.3); 7.455(1.2); 7.443(1.2);6.551(1.8); 5.753(1.3); 4.058(16.0); 3.435(14.5); 3.319(102.3);2.675(0.4); 2.671(0.5); 2.666(0.4); 2.524(1.1); 2.519(1.7); 2.511(27.9);2.506(58.4); 2.502(81.1); 2.497(59.8); 2.493(28.3); 2.333(0.4);2.329(0.5); 2.324(0.3); 1.236(0.6); 0.008(1.9); 0.000(61.1); −0.008(2.1)72 1H-NMR(400.0 MHz, DMSO): δ = 8.538(2.0); 8.532(2.1); 8.491(1.5);8.488(1.6); 8.479(1.5); 8.476(1.6); 7.898(0.8); 7.894(1.0); 7.892(1.0);7.888(0.9); 7.878(1.0); 7.874(1.1); 7.872(1.1); 7.868(0.9); 7.468(1.3);7.456(1.3); 7.448(1.2); 7.436(1.1); 7.350(6.5); 6.556(1.6); 5.754(2.6);4.431(1.2); 4.413(4.0); 4.395(4.0); 4.378(1.3); 4.010(16.0);3.423(14.7); 3.320(36.8); 2.524(0.7); 2.511(14.6); 2.507(30.3);2.502(42.3); 2.498(32.2); 1.359(4.3); 1.341(8.9); 1.323(4.2);0.008(1.9); 0.000(52.8); −0.008(1.9) 73 1H-NMR(400.0 MHz, DMSO): δ =8.600(5.3); 8.530(1.4); 8.525(1.4); 8.472(1.1); 8.461(1.1); 8.315(0.8);7.875(0.8); 7.872(1.0); 7.869(1.0); 7.865(0.8); 7.855(0.9); 7.851(1.0);7.849(1.1); 7.845(0.9); 7.456(1.1); 7.445(1.1); 7.436(1.0); 7.424(0.9);6.364(3.2); 5.754(0.5); 4.917(0.4); 4.901(1.0); 4.884(1.4); 4.867(1.0);4.850(0.4); 4.099(16.0); 3.408(14.3); 3.318(18.8); 3.295(0.3);2.671(0.4); 2.510(22.7); 2.506(45.5); 2.502(62.2); 2.497(47.1);2.493(23.5); 2.328(0.4); 1.529(14.8); 1.512(14.8); 1.235(0.5);0.008(1.0); 0.000(22.8); −0.008(0.9) 74 1H-NMR(400.0 MHz, DMSO): δ =8.537(2.0); 8.531(2.1); 8.478(1.6); 8.470(5.2); 8.463(1.7); 7.884(0.8);7.880(1.0); 7.877(1.0); 7.874(0.9); 7.863(0.9); 7.859(1.1); 7.857(1.1);7.853(0.9); 7.462(1.1); 7.451(1.2); 7.442(1.1); 7.430(1.0); 6.360(3.0);5.754(0.9); 4.102(13.9); 4.094(16.0); 3.406(14.1); 3.319(53.3);2.675(0.4); 2.671(0.6); 2.666(0.4); 2.541(0.5); 2.506(71.2);2.502(95.1); 2.497(73.3); 2.333(0.4); 2.328(0.6); 2.324(0.4);0.008(0.7); 0.000(15.1) 75 ¹H-NMR(400.0 MHz, CD3CN): δ = 8.592(2.3);8.586(2.4); 8.505(1.2); 8.501(1.3); 8.493(1.3); 8.489(1.3); 8.415(1.7);8.409(1.7); 8.231(2.6); 8.225(2.6); 8.052(0.7); 7.729(0.7); 7.725(0.8);7.723(0.8); 7.719(0.7); 7.709(0.8); 7.705(0.9); 7.702(0.9); 7.698(0.8);7.421(0.9); 7.420(1.0); 7.409(0.9); 7.408(1.0); 7.401(0.8); 7.399(0.9);7.389(0.8); 7.387(0.8); 6.337(2.5); 5.448(7.0); 4.074(16.0); 3.945(1.0);3.927(3.1); 3.909(3.1); 3.891(1.0); 3.817(15.3); 1.965(0.3); 1.958(0.6);1.953(4.3); 1.946(8.0); 1.940(11.2); 1.934(7.7); 1.928(3.9); 1.195(3.3);1.177(7.1); 1.159(3.3); 0.008(1.3); 0.000(44.8); −0.008(1.6) 76¹H-NMR(400.0 MHz, CD3CN): δ = 8.567(2.4); 8.561(2.6); 8.504(1.0);8.493(1.0); 8.412(1.3); 8.219(2.6); 8.214(2.6); 7.722(1.0); 7.706(0.9);7.702(1.1); 7.420(1.0); 7.408(1.0); 7.399(1.0); 7.387(0.9); 6.334(2.1);5.446(4.0); 4.557(1.3); 4.539(4.1); 4.521(4.2); 4.504(1.4); 3.944(1.1);3.926(3.5); 3.908(3.6); 3.890(1.2); 3.816(16.0); 1.964(0.5); 1.958(0.9);1.952(6.0); 1.946(11.4); 1.940(16.1); 1.934(11.3); 1.927(5.9);1.436(4.2); 1.418(8.5); 1.401(4.2); 1.355(0.5); 1.194(3.8); 1.177(8.0);1.159(3.8); 0.008(1.8); 0.000(59.4) 77 ¹H-NMR(400.0 MHz, CD3CN): δ =8.619(1.1); 8.617(1.1); 8.607(1.1); 8.605(1.1); 8.475(1.3); 8.471(1.4);8.463(1.4); 8.459(1.4); 8.411(1.9); 8.406(1.9); 7.986(1.4); 7.966(1.8);7.827(0.8); 7.823(0.8); 7.808(1.2); 7.804(1.2); 7.788(0.7); 7.784(0.7);7.700(0.7); 7.697(0.9); 7.694(0.8); 7.690(0.7); 7.680(0.8); 7.676(1.0);7.674(0.9); 7.670(0.8); 7.387(1.0); 7.375(1.0); 7.367(0.9); 7.355(0.9);7.349(0.9); 7.347(0.9); 7.337(0.8); 7.335(0.9); 7.331(0.9); 7.328(0.8);7.318(0.8); 7.316(0.7); 6.415(3.2); 5.447(0.7); 4.188(16.0); 3.961(1.1);3.943(3.4); 3.925(3.5); 3.907(1.1); 2.161(3.9); 1.958(0.4); 1.952(2.8);1.946(5.1); 1.940(7.2); 1.934(5.0); 1.928(2.5); 1.200(3.6); 1.182(7.4);1.165(3.5); 0.008(1.2); 0.000(28.9); −0.008(1.2) 78 ¹H-NMR(400.0 MHz,CD3CN): δ = 8.454(1.0); 8.441(1.9); 7.721(1.1); 7.715(0.8); 7.712(0.9);7.709(0.9); 7.702(2.2); 7.695(0.9); 7.691(1.0); 7.689(1.0); 7.682(1.8);7.607(2.1); 7.588(1.5); 7.379(0.9); 7.368(0.9); 7.359(0.8); 7.347(0.8);6.785(1.8); 6.764(1.7); 6.445(2.0); 5.447(1.1); 4.225(15.9);3.960(16.0); 3.437(15.7); 2.183(0.7); 1.958(0.5); 1.952(3.5);1.946(6.6); 1.940(9.0); 1.934(6.2); 1.928(3.1); 0.000(7.3) 79¹H-NMR(400.0 MHz, CD3CN): δ = 8.489(0.6); 8.486(0.6); 8.477(0.6);8.474(0.6); 8.451(0.8); 8.445(0.9); 7.733(0.4); 7.731(0.4); 7.727(0.3);7.716(0.4); 7.713(0.4); 7.710(0.4); 7.706(0.4); 7.412(0.5); 7.400(0.5);7.391(0.4); 7.379(0.4); 7.346(0.5); 7.343(0.5); 7.327(0.6); 7.324(0.6);7.147(0.5); 7.128(0.6); 6.934(0.7); 6.915(1.0); 6.896(0.5); 6.351(1.6);5.446(2.4); 4.620(1.1); 4.598(2.1); 4.576(1.2); 3.661(7.8); 3.417(7.7);3.285(0.7); 3.263(1.2); 3.241(0.6); 2.626(1.0); 2.147(4.5); 1.957(0.4);1.951(3.3); 1.945(6.2); 1.939(8.6); 1.933(5.9); 1.927(3.0); 1.200(0.5);1.134(16.0); 0.000(4.1) 80 ¹H-NMR(400.0 MHz, CD3CN): δ = 8.511(0.5);8.508(0.6); 8.494(0.9); 8.487(0.8); 7.801(1.0); 7.795(1.2); 7.789(0.6);7.773(0.8); 7.770(0.9); 7.762(0.3); 7.751(0.4); 7.748(0.4); 7.745(0.4);7.433(0.4); 7.420(0.7); 7.416(0.6); 7.401(1.1); 7.378(0.7); 7.359(0.9);6.959(1.1); 6.954(1.0); 6.448(1.2); 5.447(1.3); 3.711(5.8); 3.454(0.7);3.445(5.7); 3.285(0.7); 2.627(1.6); 2.149(4.6); 1.952(2.5); 1.945(4.6);1.939(6.1); 1.933(4.2); 1.927(2.1); 1.199(0.5); 1.134(16.0); 0.000(2.9)81 ¹H-NMR(400.0 MHz, CD3CN): δ = 8.492(1.2); 8.488(1.3); 8.480(1.3);8.476(1.3); 8.454(1.7); 8.449(1.8); 8.043(0.4); 7.735(0.7); 7.731(0.8);7.728(0.8); 7.725(0.7); 7.714(0.8); 7.711(1.0); 7.708(0.9); 7.704(0.8);7.586(2.4); 7.565(2.5); 7.414(1.0); 7.402(1.0); 7.394(0.9); 7.382(0.9);6.431(2.7); 6.411(2.6); 6.352(3.0); 5.447(2.4); 3.954(16.0);3.943(15.4); 3.584(15.5); 3.417(15.3); 1.963(0.4); 1.957(0.9);1.952(5.6); 1.945(10.4); 1.939(14.2); 1.933(9.7); 1.927(4.9); 0.000(6.1)82 ¹H-NMR(400.0 MHz, CD3CN): δ = 8.498(0.4); 8.487(0.4); 8.466(0.5);8.462(0.5); 7.733(0.3); 7.712(0.4); 7.710(0.4); 7.485(0.4); 7.418(0.4);7.406(0.4); 7.398(0.3); 7.386(0.3); 7.279(0.4); 7.276(0.4); 7.260(0.4);7.257(0.4); 7.107(0.6); 7.086(0.6); 7.053(0.3); 7.034(0.6); 6.352(0.4);5.446(2.0); 3.806(5.2); 3.566(3.5); 3.421(5.5); 2.626(1.4); 2.146(2.4);1.951(2.4); 1.945(4.5); 1.939(6.0); 1.933(4.2); 1.927(2.1); 1.134(16.0);0.000(3.3) 83 ¹H-NMR(400.0 MHz, CD3CN): δ = 8.491(1.6); 8.488(1.5);8.479(1.6); 8.476(1.6); 8.455(2.2); 8.449(2.2); 8.029(1.1); 7.743(0.9);7.739(1.1); 7.736(1.0); 7.733(0.8); 7.722(1.0); 7.718(1.2); 7.413(1.2);7.401(1.2); 7.393(1.1); 7.381(1.0); 6.972(0.5); 6.961(1.2); 6.959(1.3);6.948(2.8); 6.939(1.0); 6.929(4.3); 6.927(3.7); 6.916(3.3); 6.383(3.5);6.024(10.7); 5.447(3.3); 3.730(16.0); 3.421(15.8); 1.963(0.4);1.951(5.0); 1.945(9.2); 1.939(12.2); 1.933(8.5); 1.927(4.3); 0.000(3.7)84 ¹H-NMR(400.0 MHz, CD3CN): δ = 8.490(1.5); 8.486(1.5); 8.478(1.5);8.475(1.4); 8.453(2.0); 8.447(2.0); 7.728(0.9); 7.725(1.0); 7.722(0.9);7.718(0.8); 7.708(1.0); 7.704(1.1); 7.702(1.1); 7.698(0.8); 7.411(1.1);7.400(1.1); 7.391(1.0); 7.379(0.9); 7.192(2.3); 7.171(2.5); 6.625(2.1);6.619(2.8); 6.603(1.8); 6.598(1.1); 6.582(1.5); 6.577(1.1); 6.321(3.7);3.836(15.8); 3.793(15.0); 3.548(16.0); 3.414(16.0); 2.763(0.5);2.750(0.5); 2.144(8.7); 1.963(0.6); 1.951(7.4); 1.945(13.3);1.939(17.6); 1.933(12.0); 1.927(6.1); 1.199(2.4); 1.134(1.4); 0.000(1.9)85 ¹H-NMR(400.0 MHz, CD3CN): δ = 8.492(0.9); 8.481(1.0); 8.458(1.3);8.452(1.3); 7.728(0.7); 7.726(0.6); 7.712(0.6); 7.708(0.7); 7.414(0.7);7.403(0.7); 7.394(0.7); 7.382(0.6); 7.030(1.8); 7.025(3.4); 6.835(1.4);6.829(1.2); 6.349(2.1); 5.447(2.1); 5.445(2.0); 3.742(16.0); 3.571(8.1);3.570(7.8); 3.419(8.1); 3.418(7.7); 2.763(0.4); 2.750(0.4); 2.632(0.8);2.151(6.3); 1.950(3.8); 1.945(6.2); 1.944(6.7); 1.939(8.3); 1.938(8.3);1.933(5.8); 1.931(5.6); 1.927(3.0); 1.199(1.3); 1.134(8.9); 1.132(8.3);0.000(0.9); −0.002(0.9) 86 ¹H-NMR(400.0 MHz, CD3CN): δ = 8.457(1.6);8.454(1.6); 8.443(3.5); 8.437(2.2); 8.263(1.6); 8.243(1.9); 8.058(1.0);8.038(1.8); 8.018(0.9); 7.766(2.0); 7.747(1.7); 7.718(0.9); 7.714(1.0);7.712(1.0); 7.708(0.8); 7.698(1.0); 7.694(1.1); 7.691(1.1); 7.688(0.8);7.378(1.2); 7.366(1.2); 7.358(1.1); 7.346(1.0); 6.504(3.0); 4.212(16.0);3.444(15.9); 2.163(4.5); 1.964(0.5); 1.952(6.3); 1.946(11.3);1.940(14.8); 1.934(10.1); 1.928(5.1); 0.000(1.3) 87 ¹H-NMR(400.0 MHz,CD3CN): δ = 8.497(1.3); 8.493(1.3); 8.485(1.4); 8.481(1.2); 8.454(1.8);8.449(1.8); 8.276(2.6); 8.269(2.6); 7.735(0.8); 7.732(0.9); 7.729(0.9);7.725(0.8); 7.714(3.6); 7.708(3.4); 7.417(1.0); 7.405(1.0); 7.396(0.9);7.384(0.9); 6.391(2.7); 5.447(4.0); 3.923(16.0); 3.606(15.7);3.422(15.6); 1.964(0.6); 1.957(1.4); 1.952(6.5); 1.946(11.6);1.940(15.3); 1.933(10.3); 1.927(5.1); 0.000(1.4) 88 ¹H-NMR(400.0 MHz,CD3CN): δ = 8.497(1.4); 8.494(1.4); 8.485(1.5); 8.482(1.5); 8.461(2.0);8.455(2.0); 8.295(1.3); 8.290(1.4); 8.283(1.4); 8.278(1.4); 8.033(1.6);7.742(0.8); 7.738(1.0); 7.736(1.0); 7.732(0.8); 7.722(0.9); 7.718(1.1);7.716(1.1); 7.712(0.9); 7.694(1.4); 7.689(1.5); 7.676(1.6); 7.671(1.5);7.418(1.1); 7.406(1.1); 7.398(1.0); 7.386(0.9); 7.063(1.4); 7.050(1.5);7.044(1.4); 7.032(1.3); 6.381(3.1); 5.447(2.2); 3.927(16.0);3.594(15.6); 3.424(15.6); 2.761(1.5); 1.964(0.5); 1.952(5.8);1.946(10.8); 1.939(14.7); 1.933(10.2); 1.927(5.3); 1.199(1.1);1.134(2.1); 0.000(6.8) 89 ¹H-NMR(400.0 MHz, CD3CN): δ = 8.482(1.4);8.478(1.4); 8.470(1.5); 8.466(1.4); 8.456(2.0); 8.450(2.0); 8.347(1.9);8.340(2.0); 7.854(1.4); 7.848(1.4); 7.832(1.6); 7.826(1.5); 7.736(0.8);7.733(0.9); 7.730(0.8); 7.726(0.7); 7.716(0.9); 7.712(1.0); 7.706(0.8);7.404(1.1); 7.393(1.1); 7.384(1.0); 7.372(1.0); 6.824(2.2); 6.803(2.1);6.361(3.5); 4.406(1.2); 4.388(3.9); 4.370(3.9); 4.361(0.4); 4.353(1.3);3.813(16.0); 3.421(15.7); 2.764(1.1); 2.751(1.1); 2.625(1.0);2.147(8.7); 1.964(0.5); 1.958(1.2); 1.952(7.5); 1.946(13.8);1.940(18.7); 1.933(12.7); 1.927(6.5); 1.380(4.1); 1.362(8.1);1.345(4.0); 1.322(0.3); 1.312(3.8); 1.201(1.2); 1.134(11.8) 90¹H-NMR(400.0 MHz, CD3CN): δ = 8.481(1.2); 8.469(1.2); 8.453(1.6);8.448(1.7); 8.302(2.4); 8.297(2.6); 7.962(2.8); 7.957(2.9); 7.740(0.7);7.736(0.9); 7.733(0.9); 7.730(0.8); 7.719(0.8); 7.716(1.0); 7.713(1.0);7.709(0.9); 7.407(1.0); 7.395(1.0); 7.387(0.9); 7.375(0.9); 6.376(2.8);5.447(7.0); 4.024(16.0); 3.826(15.7); 3.422(15.4); 1.964(0.5);1.958(0.9); 1.952(5.8); 1.946(10.9); 1.940(15.1); 1.934(10.4);1.928(5.4) 91 ¹H-NMR(400.0 MHz, CD3CN): δ = 8.552(1.3); 8.547(1.4);8.539(1.4); 8.535(1.4); 8.501(1.0); 8.490(1.1); 8.469(1.3); 7.735(0.8);7.731(0.9); 7.729(0.9); 7.725(0.7); 7.715(0.9); 7.711(1.0); 7.709(1.0);7.705(0.8); 7.556(1.1); 7.552(1.1); 7.537(1.2); 7.533(1.2); 7.416(0.9);7.405(1.0); 7.396(0.9); 7.384(0.8); 7.179(1.3); 7.167(1.3); 7.160(1.2);7.148(1.1); 6.416(1.1); 5.447(3.1); 3.590(12.7); 3.429(15.8);2.765(0.5); 2.752(0.5); 2.622(0.7); 2.483(16.0); 2.145(19.4);1.964(0.6); 1.952(8.2); 1.946(15.1); 1.939(20.4); 1.933(14.1);1.927(7.3); 1.332(0.4); 1.201(0.8); 1.134(8.5) 92 ¹H-NMR(400.0 MHz,CD3CN): δ = 8.488(1.9); 8.477(2.0); 8.452(2.5); 8.447(2.5); 8.264(1.6);8.260(1.6); 8.252(1.7); 7.728(1.3); 7.708(1.5); 7.685(1.6); 7.667(1.7);7.410(1.3); 7.399(1.4); 7.390(1.2); 7.378(1.2); 7.038(1.4); 7.026(1.6);7.020(1.5); 7.008(1.3); 6.366(3.7); 5.447(1.4); 4.431(1.3); 4.413(3.9);4.396(4.0); 4.378(1.3); 3.616(15.8); 3.423(16.0); 3.020(0.4);2.149(11.9); 1.951(6.0); 1.945(10.7); 1.939(13.9); 1.933(9.7);1.927(5.0); 1.332(4.1); 1.315(8.1); 1.297(4.1); 1.270(0.3) 93¹H-NMR(400.0 MHz, CD3CN): δ = 8.482(1.2); 8.480(1.2); 8.471(1.2);8.468(1.2); 8.456(1.8); 8.450(1.7); 7.892(2.2); 7.888(2.1); 7.737(0.8);7.716(0.9); 7.408(1.0); 7.396(1.0); 7.387(0.9); 7.375(0.8); 7.343(2.2);7.338(2.1); 6.366(2.9); 5.447(2.8); 3.961(12.8); 3.836(16.0);3.424(12.4); 2.151(16.4); 1.964(0.5); 1.952(7.2); 1.946(13.1);1.940(17.7); 1.934(12.1); 1.928(6.2) 94 ¹H-NMR(400.0 MHz, CD3CN): δ =8.481(1.4); 8.478(1.4); 8.469(1.5); 8.466(1.4); 8.448(2.0); 8.442(2.0);8.231(2.0); 8.218(2.1); 8.032(0.4); 7.732(0.8); 7.728(0.9); 7.726(0.9);7.722(0.7); 7.712(0.9); 7.708(1.1); 7.705(1.0); 7.702(0.8); 7.400(1.1);7.389(1.1); 7.380(1.0); 7.368(1.0); 7.171(1.7); 7.168(1.6); 7.158(1.6);7.155(1.6); 6.968(3.0); 6.411(3.1); 5.447(0.5); 3.924(15.6);3.872(16.0); 3.425(15.6); 1.964(0.4); 1.958(0.9); 1.952(5.6);1.946(10.3); 1.940(14.2); 1.934(9.7); 1.927(5.0); 0.000(6.2) 95¹H-NMR(400.0 MHz, CD3CN): δ = 8.583(1.6); 8.579(1.6); 8.485(1.2);8.481(1.3); 8.473(1.3); 8.469(1.3); 8.456(1.7); 8.450(1.8); 8.162(1.6);8.157(1.6); 8.032(1.0); 7.744(0.7); 7.740(0.8); 7.738(0.8); 7.734(0.7);7.723(0.8); 7.720(0.9); 7.717(0.9); 7.713(0.8); 7.409(1.0); 7.397(1.0);7.389(0.9); 7.377(0.9); 6.393(3.0); 5.448(10.1); 4.059(16.0);3.836(15.4); 3.427(15.2); 1.958(0.5); 1.953(3.7); 1.946(6.9);1.940(9.5); 1.934(6.4); 1.928(3.3); 0.000(3.8) 96 ¹H-NMR(400.0 MHz,CD3CN): δ = 8.653(2.6); 8.648(2.8); 8.496(2.9); 8.491(3.1); 8.475(1.8);8.472(1.7); 8.459(2.3); 8.453(2.3); 8.024(5.7); 7.747(0.9); 7.742(1.1);7.738(0.8); 7.727(1.0); 7.721(1.2); 7.718(0.9); 7.412(1.2); 7.400(1.2);7.391(1.1); 7.380(1.0); 6.409(3.3); 5.447(6.5); 4.112(16.0);3.857(15.6); 3.430(15.4); 2.158(0.8); 2.153(0.8); 2.119(0.7);2.113(0.7); 2.107(0.7); 2.101(0.7); 1.964(1.0); 1.952(12.1);1.946(22.2); 1.940(30.0); 1.934(21.2); 1.927(11.4); 0.000(0.4) 97¹H-NMR(400.0 MHz, CD3CN): δ = 8.479(0.5); 8.468(0.5); 8.441(0.7);7.727(0.4); 7.723(0.5); 7.721(0.5); 7.717(0.4); 7.707(0.5); 7.703(0.5);7.700(0.5); 7.697(0.4); 7.400(0.5); 7.388(0.5); 7.379(0.4); 7.367(0.4);6.524(5.3); 6.385(1.3); 5.447(1.2); 3.922(16.0); 3.877(0.5); 3.849(8.2);3.419(8.1); 2.152(0.9); 1.952(2.9); 1.946(5.3); 1.940(7.2); 1.934(5.0);1.927(2.6); 0.000(1.2) 98 ¹H-NMR(400.0 MHz, CD3CN): δ = 8.491(0.3);8.488(0.4); 8.479(0.4); 8.476(0.4); 8.463(0.5); 8.457(0.5); 7.396(0.6);7.376(0.5); 7.251(0.4); 7.248(0.4); 7.233(0.8); 7.229(0.6); 6.374(0.8);5.447(0.8); 3.559(3.9); 3.425(3.9); 2.629(1.2); 2.382(3.7); 2.150(2.3);1.952(1.8); 1.945(3.3); 1.939(4.6); 1.933(3.2); 1.927(1.7); 1.134(16.0);0.000(1.0) 99 ¹H-NMR(400.0 MHz, CD3CN): δ = 8.481(1.3); 8.478(1.3);8.470(1.4); 8.467(1.3); 8.446(1.9); 8.440(1.9); 7.734(0.8); 7.730(1.0);7.728(0.9); 7.724(0.8); 7.714(0.9); 7.710(1.1); 7.707(1.1); 7.704(0.9);7.604(3.1); 7.401(1.1); 7.389(1.1); 7.380(1.0); 7.368(1.0); 7.219(3.0);6.447(2.7); 5.447(2.1); 3.979(15.7); 3.904(16.0); 3.430(15.7);2.138(5.8); 1.964(0.6); 1.952(8.2); 1.946(15.1); 1.940(20.1);1.934(13.8); 1.927(7.1); 0.000(4.5) 100 ¹H-NMR(400.0 MHz, CD3CN): δ =8.485(1.4); 8.482(1.5); 8.473(1.5); 8.470(1.6); 8.453(2.1); 8.447(2.2);8.028(0.7); 7.740(0.8); 7.736(1.0); 7.734(1.0); 7.730(0.9); 7.720(1.0);7.714(1.2); 7.710(1.0); 7.517(3.2); 7.406(2.8); 7.399(2.3); 7.387(1.2);7.375(1.1); 7.363(2.0); 7.360(2.2); 7.354(1.7); 6.392(3.3); 5.447(5.3);3.861(15.8); 3.839(16.0); 3.426(15.9); 2.151(0.4); 2.135(0.3);2.113(0.3); 2.107(0.3); 1.964(0.5); 1.952(6.2); 1.946(11.6);1.940(15.8); 1.934(11.2); 1.927(5.9); 0.000(3.1) 101 ¹H-NMR(400.0 MHz,CD3CN): δ = 8.496(1.4); 8.493(1.4); 8.485(1.5); 8.481(1.4); 8.455(1.9);8.449(1.9); 8.180(2.4); 8.172(2.4); 7.738(0.8); 7.734(0.9); 7.731(0.9);7.728(0.8); 7.718(0.9); 7.714(1.1); 7.711(1.0); 7.707(0.8); 7.562(1.3);7.554(1.3); 7.541(1.4); 7.534(1.3); 7.417(1.1); 7.405(1.1); 7.396(1.0);7.384(1.0); 6.387(2.9); 5.447(5.1); 3.914(16.0); 3.611(15.9);3.423(15.6); 2.166(0.4); 2.156(0.4); 1.964(0.6); 1.952(6.0);1.946(10.9); 1.939(14.7); 1.933(10.1); 1.927(5.3); 0.000(2.0) 102¹H-NMR(400.0 MHz, d₆-DMSO): δ = 8.541(2.1); 8.535(2.2); 8.501(1.5);8.498(1.6); 8.489(1.7); 8.486(1.6); 8.416(2.3); 8.411(2.4); 8.138(2.1);7.948(1.5); 7.942(1.4); 7.927(1.6); 7.921(1.5); 7.901(0.9); 7.898(1.1);7.895(1.0); 7.891(0.9); 7.881(1.0); 7.877(1.1); 7.875(1.1); 7.871(0.9);7.487(1.1); 7.475(1.2); 7.466(1.1); 7.454(1.0); 6.852(2.2); 6.830(2.2);6.356(3.5); 5.757(5.6); 5.331(0.4); 5.315(1.2); 5.300(1.6); 5.284(1.2);5.269(0.5); 3.826(14.7); 3.405(13.9); 3.323(1.3); 2.507(33.2);2.502(42.2); 2.498(31.1); 1.321(16.0); 1.306(15.9); 1.285(0.9);1.270(0.6); 0.000(0.9) 103 ¹H-NMR(400.0 MHz, CD3CN): δ = 8.482(1.4);8.479(1.4); 8.470(1.5); 8.467(1.4); 8.457(2.0); 8.451(2.0); 8.370(1.9);8.365(2.0); 7.865(1.4); 7.859(1.3); 7.844(1.4); 7.838(1.4); 7.738(0.8);7.734(0.9); 7.732(0.9); 7.728(0.7); 7.718(0.9); 7.714(1.0); 7.711(1.0);7.708(0.8); 7.406(1.0); 7.394(1.1); 7.385(1.0); 7.373(0.9); 6.865(2.0);6.843(1.9); 6.364(3.4); 3.936(16.0); 3.815(15.5); 3.422(15.2);2.156(8.4); 1.964(0.6); 1.952(7.0); 1.946(12.8); 1.940(17.1);1.934(11.9); 1.927(6.1); 0.000(0.7) 104 ¹H-NMR(400.0 MHz, CD3CN): δ =8.496(1.4); 8.486(1.5); 8.468(2.1); 8.462(2.1); 8.030(0.4); 7.747(1.0);7.726(1.2); 7.507(0.7); 7.503(0.7); 7.484(1.4); 7.467(0.9); 7.463(0.9);7.420(1.2); 7.408(1.2); 7.400(1.1); 7.388(1.0); 7.367(1.4); 7.364(1.4);7.348(1.7); 7.345(1.6); 7.298(0.4); 7.136(1.1); 7.117(1.9); 7.102(2.4);7.082(1.8); 6.451(0.3); 6.388(2.7); 5.897(0.4); 4.498(9.6); 3.946(1.6);3.686(14.2); 3.430(16.0); 3.417(1.9); 2.298(0.5); 2.183(1.0);2.179(1.0); 2.113(0.6); 2.107(0.6); 2.101(0.5); 1.964(9.7); 1.952(8.6);1.946(15.3); 1.939(20.5); 1.933(14.5); 1.927(7.7); 1.134(2.1);0.000(0.5) 105 ¹H-NMR(400.0 MHz, CD3CN): δ = 8.481(1.5); 8.477(1.4);8.469(1.6); 8.465(1.4); 8.451(2.0); 8.445(2.0); 7.826(2.0); 7.821(2.9);7.807(1.7); 7.801(1.0); 7.785(1.6); 7.779(1.2); 7.732(0.9); 7.729(1.0);7.726(0.9); 7.722(0.7); 7.712(1.0); 7.708(1.1); 7.705(1.1); 7.702(0.8);7.403(1.1); 7.391(1.1); 7.382(1.0); 7.370(1.0); 7.217(2.1); 7.195(2.0);6.349(3.5); 5.447(3.6); 4.842(0.4); 4.827(1.0); 4.812(1.3); 4.797(1.0);4.782(0.4); 3.811(16.0); 3.420(15.7); 2.148(7.5); 1.952(4.8);1.946(9.0); 1.940(12.3); 1.934(8.4); 1.927(4.2); 1.390(15.6);1.375(15.4); 1.312(0.5); 1.297(0.5); 0.008(1.5); 0.000(36.5);−0.009(1.4) 106 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 8.670(1.6); 8.667(2.0);8.658(1.8); 8.655(2.0); 8.565(2.5); 8.559(2.6); 8.508(1.5); 8.504(1.9);8.496(1.7); 8.493(1.9); 8.135(1.7); 8.132(2.0); 8.114(1.9); 8.111(2.1);7.911(0.8); 7.908(1.1); 7.905(1.2); 7.902(1.0); 7.891(1.0); 7.887(1.2);7.885(1.3); 7.881(1.1); 7.596(1.7); 7.585(1.6); 7.576(1.6); 7.564(1.5);7.489(1.3); 7.478(1.4); 7.469(1.3); 7.457(1.2); 6.424(2.7); 3.701(16.0);3.419(15.0); 3.322(10.9); 2.956(0.4); 2.671(0.4); 2.506(42.3);2.502(57.2); 2.497(45.9); 2.328(0.3); 0.007(2.1); 0.000(49.3)

Use Examples

Meloidogyne Incognita Test

Solvent: 125.0 parts by weight of acetone

To produce a suitable active compound formulation, 1 part by weight ofactive compound is mixed with the stated amount of solvent and theconcentrate is diluted with water to the desired concentration.

Vessels are filled with sand, active compound solution, an egg/larvaesuspension of the southern root-knot nematode (Meloidogyne incognita)and lettuce seeds. The lettuce seeds germinate and the plants develop.The galls develop on the roots.

After 14 days, the nematicidal efficacy in % is determined by theformation of galls. 100% means that no galls were found; 0% means thatthe number of galls on the treated plants corresponds to the untreatedcontrol.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 20 ppm: 83

Tetranychus Urticae—Spray Test, OP-Resistant

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the specified parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the formulation is diluted withemulsifier-containing water.

Discs of bean leaves (Phaseolus vulgaris) infested with all stages ofthe greenhouse red spider mite (Tetranychus urticae) are sprayed with anactive compound formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all thespider mites have been killed; 0% means that no spider mites have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 500 g/ha:105

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 500 g/ha: 52,57, 72

Myzus persicae—Spray Test

Solvent: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the specified parts by weight ofsolvent and made up with water containing an emulsi fier concentrationof 1000 ppm until the desired concentration is attained. To producefurther test concentrations, the formulation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive compound formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 500 g/ha: 1,6, 9, 16, 21, 22, 23, 33, 38, 48, 52, 57, 58, 61, 62, 65, 67, 68, 69,71, 73, 74, 75, 77, 79, 80, 81, 82, 84, 87, 95, 97, 101, 103, 104

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 500 g/ha: 2,3, 4, 5, 7, 10, 11, 13, 14, 15, 17, 18, 19, 20, 24, 25, 26, 27, 28, 29,30, 31, 32, 35, 36, 37, 39, 40, 44, 45, 47, 53, 54, 55, 56, 59, 60, 63,64, 66, 76, 78, 83, 86, 88, 89, 90, 91, 92, 93, 94, 99, 100, 102, 105,106

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 100 g/ha: 8

Myzus persicae—Oral Test

Solvent: 100 parts by weight of acetone

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the specified parts by weight ofsolvent and made up with water until the desired concentration isattained.

50 μl of the active compound preparation are transferred into microtitreplates and made up to a final volume of 200 μl with 150 μl of IPL41insect medium (33%+15% sugar). Subsequently, the plates are sealed withparafilm, which a mixed population of green peach aphids (Myzuspersicae) within a second microtitre plate is able to puncture andimbibe the solution through it.

After 5 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 20 ppm: 1,2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 21, 22, 23,24, 25, 26, 27, 28, 29, 30, 33, 36, 38, 39, 46, 47, 48, 49, 50, 51, 52,53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70,71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88,89, 90, 91, 92, 93, 94, 95, 97, 98, 99, 100, 101, 102, 103, 104, 105

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 20 ppm: 19,32, 35, 37, 44, 45, 106

Myzus persicae—Spray Test

Solvent: 14 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the specified parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the formulation is diluted withemulsifier-containing water. If the addition of ammonium salts or/andpenetrants is required, these are each added in a concentration of 1000ppm to the formulation solution.

Bell pepper plants (Capsicum annuum) severely infested with the greenpeach aphid (Myzus persicae) are treated by spraying with the activecompound formulation in the desired concentration.

After 6 days, the kill in % is determined. 100% means that all of theaphids have been killed; 0% means that none of the aphids have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 20 ppm: 12,49, 50, 51, 77

In this test, for example, the following compounds from the preparationexamples show an efficacy of 95% at an application rate of 20 ppm: 46,70

Deposition Examples

Myzus persicae—Spray Test (MYZUPE)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the specified parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the formulation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive compound preparation of the desired concentration.

After the desired period of time, the efficacy in % is determined. 100%means that all the aphids have been killed; 0% means that no aphids havebeen killed.

In this test, for example, the following compounds of the preparationexamples show superior efficacy to the prior art: see Table 3

Myzus persicae—Oral Test (MYZUPE O)

Solvent: 100 parts by weight of acetone

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the specified parts by weight ofsolvent and made up with water until the desired concentration isattained.

50 μl of the active compound preparation are transferred into microtitreplates and made up to a final volume of 200 μl with 150 μl of IPL41insect medium (33%+15% sugar). Subsequently, the plates are sealed withparafilm, which a mixed population of green peach aphids (Myzuspersicae) within a second microtitre plate is able to puncture andimbibe the solution through it.

After 5 or 6 days (dat), the efficacy in % is determined. 100% meansthat all the aphids have been killed; 0% means that no aphids have beenkilled.

In this test, for example, the following compounds of the preparationexamples show superior efficacy to the prior art: see Table 3

TABLE 3 Animal Substance Structure species Concentration % efficacy datComparative Ex. 1 WO2011/009804

MYZUPE MYZUPE O 100 g ai/ha 4 ppm  0 5/6 dat  0 5 dat Comparative Ex. 2WO2011/009804

MYZUPE MYZUPE O 100 g ai/ha 4 ppm  0 6 dat  0 5 dat Ex. No. 1 accordingto the invention

MYZUPE O 4 ppm 100 5 dat Ex. No. 4 according to the invention

MYZUPE MYZUPE O 100 g ai/ha 4 ppm  90 6 dat 100 5 dat Ex. No. 6according to the invention

MYZUPE MYZUPE O 100 g ai/ha 4 ppm  90 6 dat 100 5 dat Ex. No. 11according to the invention

MYZUPE MYZUPE O 100 g ai/ha 4 ppm  90 6 dat 100 5 dat Ex. No. 16according to the invention

MYZUPE MYZUPE O 100 g ai/ha 4 ppm  90 6 dat 100 5 dat Ex. No. 55according to the invention

MYZUPE MYZUPE O 100 g ai/ha 4 ppm  90 6 dat 100 5 dat Ex. No. 64according to the invention

MYZUPE MYZUPE O 100 g ai/ha 4 ppm  90 5 dat 100 5 dat Ex. No. 65according to the invention

MYZUPE MYZUPE O 100 g ai/ha 4 ppm  90 5 dat 100 5 dat Ex. No. 68according to the invention

MYZUPE MYZUPE O 100 g ai/ha 4 ppm 100 5 dat 100 5 dat Ex. No. 78according to the invention

MYZUPE MYZUPE O 100 g ai/ha 4 ppm  70 5 dat 100 5 dat Ex. No. 81according to the invention

MYZUPE MYZUPE O 100 g ai/ha 4 ppm  70 5 dat  70 5 dat Ex. No. 87according to the invention

MYZUPE MYZUPE O 100 g ai/ha 4 ppm  90 5 dat 100 5 dat Ex. No. 99according to the invention

MYZUPE MYZUPE O 100 g ai/ha 4 ppm  70 5 dat 100 5 dat

The invention claimed is:
 1. An intermediate of formula (X),

wherein Q represents oxygen or sulphur, V represents a radical selectedfrom the group consisting of hydrogen, halogen, alkyl, haloalkyl,alkoxy, haloalkoxy and cyano, W represents a radical selected from thegroup consisting of hydrogen, halogen, alkyl, haloalkyl, alkoxy,haloalkoxy and cyano, X represents a radical selected from the groupconsisting of Cl, Br, I, and ethinyl, Y represents a radical selectedfrom the group consisting of hydrogen, cyano, optionally substitutedalkyl, alkenyl or alkynyl, optionally substituted cycloalkyl which isoptionally interrupted by heteroatoms and optionally substitutedcycloalkylalkyl which is optionally interrupted by heteroatoms,arylalkyl or hetarylalkyl, A represents a radical selected from thegroup consisting of hydrogen, optionally substituted alkyl, alkenyl oralkynyl and cycloalkyl or cycloalkylalkyl, optionally interrupted byheteroatoms and optionally substituted, T represents oxygen or anelectron pair, and/or a salt thereof.
 2. The intermediate of formula (X)according to claim 1, wherein X is Cl.
 3. The intermediate of formula(X) according to claim 1, wherein X is Br.
 4. The intermediate offormula (X) according to claim 1, wherein X is I.
 5. The intermediate offormula (X) according to claim 1, wherein X is ethinyl.
 6. Theintermediate of formula (X) according to claim 1, wherein Q representsoxygen or sulphur, V represents a radical selected from the groupconsisting of hydrogen, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and cyano, W represents a radicalselected from the group consisting of hydrogen, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and cyano, Y representsa radical selected from the group consisting of hydrogen, methyl, cyano,C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally mono- topolysubstituted independently of one another by halogen, C₁-C₄-alkoxy,C₁-C₄-alkyl-S(O)_(m)- or cyano, C₃-C₈-cycloalkyl, optionally mono- todisubstituted independently of one another by halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or cyano, straight-chain or branchedC₃-C₈-cycloalkyl-C₁-C₄-alkyl, optionally interrupted once to twiceindependently of one another by O, S(O)_(m), CO or NR² and optionallymono-to tetrasubstituted independently of one another by halogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or cyano, and arylalkyl orhetarylalkyl, optionally mono- to trisubstituted independently of oneanother by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-alkyl-S(O)_(m)-, C₁-C₄-haloalkoxy, C₁-C₄-haloalkyl-S(O)_(m)-,nitro or cyano, m represents a number 0, 1 or 2, A represents a radicalfrom the group consisting of hydrogen, methyl, C₁-C₆-alkyl,C₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally mono- to polysubstitutedindependently of one another by halogen, C₁-C₄-alkoxy,C₁-C₄-alkyl-S(O)_(m)- or cyano and C₃-C₆-cycloalkyl, optionally mono- todisubstituted independently of one another by halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or cyano and straight-chain or branchedC₃-C₈-cycloalkyl-C₁-C₄-alkyl, optionally mono- to disubstitutedindependently of one another by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or cyano, R² represents a radical from the group consistingof hydrogen, optionally substituted alkyl, alkenyl, alkynyl andcycloalkyl, T represents oxygen or an electron pair, and/or a saltthereof.
 7. The intermediate of formula (X) according to claim 1,wherein Q represents oxygen or sulphur, V represents a radical selectedfrom the group consisting of hydrogen, fluorine, chlorine, bromine,methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy,difluoromethoxy, trifluoromethoxy and cyano, W represents a radicalselected from the group consisting of hydrogen, fluorine, chlorine,bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy,ethoxy, difluoromethoxy, trifluoromethoxy and cyano, Y represents aradical selected from the group consisting of hydrogen, cyano,C₁-C₄-alkyl, C₃-C₄-alkenyl or C₃-C₄-alkynyl, optionally mono- topentasubstituted independently of one another by fluorine, chlorine,bromine, methoxy, ethoxy, methyl-S(O)_(m)-, ethyl-S(O)_(m)- or cyano,C₃-C₆-cycloalkyl, optionally mono- to disubstituted independently of oneanother by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,methoxy, ethoxy or cyano, and straight-chain or branchedC₃-C₆-cycloalkyl-C₁-C₂-alkyl, optionally interrupted once to twiceindependently of one another by O, S(O)_(m)CO or NR² and optionallymono-to tetrasubstituted independently of one another by fluorine,chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy orcyano, m represents a number 0, 1 or 2, A represents a radical selectedfrom the group consisting of hydrogen, methyl, C₁-C₆-alkyl,C₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally mono- to pentasubstitutedindependently of one another by fluorine, chlorine, bromine, methoxy,ethoxy, methyl-S(O)_(m), ethyl-S(O)_(m)- or cyano, C₃-C₆-cycloalkyl,optionally mono- to disubstituted independently of one another byfluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy,ethoxy or cyano, and straight-chain or branchedC₃-C₆-cycloalkyl-C₁-C₂-alkyl, optionally mono- to disubstitutedindependently of one another by fluorine, chlorine, bromine, methyl,ethyl, trifluoromethyl, methoxy, ethoxy or cyano, R² represents aradical selected from the group consisting of hydrogen, optionallysubstituted alkyl, alkenyl, alkynyl and cycloalkyl, T represents oxygenor an electron pair, and/or a salt thereof.
 8. The intermediate offormula (X) according to claim 1, wherein Q represents oxygen orsulphur, V represents a radical selected from the group consisting ofhydrogen, fluorine, chlorine, methyl and cyano, W represents a radicalselected from the group consisting of hydrogen, fluorine, chlorine,bromine, methyl, ethyl and cyano, Y represents a radical selected fromthe group consisting of hydrogen, benzyl and methyl, ethyl, propyl,allyl or propargyl, optionally mono- to trisubstituted independently ofone another by fluorine, methoxy, ethoxy or cyano, m represents a number0, 1 or 2, A represents a radical selected from the group consisting ofhydrogen, methyl, ethyl, propyl, allyl, propargyl, cyclopropyl orcyclopropylmethyl, optionally mono- to trisubstituted independently ofone another by fluorine, methoxy, ethoxy or cyano, T represents oxygenor an electron pair, and/or a salt thereof.
 9. The intermediate offormula (X) according according to claim 8, wherein Q represents oxygenor sulphur, V represents hydrogen or fluorine, W represents a radicalselected from the group consisting of hydrogen, chlorine, bromine andmethyl, Y represents a radical selected from the group consisting ofhydrogen, methyl, ethyl, propyl, difluoroethyl, trifluoroethyl,methoxymethyl, ethoxymethyl, cyanomethyl and benzyl, m represents anumber 0, 1 or 2, A represents a radical selected from the groupconsisting of hydrogen, methyl, ethyl, propyl, difluoroethyl,trifluoroethyl, methoxymethyl, ethoxymethyl, cyanomethyl, allyl,propargyl, cyclopropyl and cyclopropylmethyl, T represents oxygen or anelectron pair, and/or a salt thereof.
 10. The intermediate of formula(X) according to claim 8, wherein Q represents oxygen or sulphur, Vrepresents hydrogen, W represents a radical selected from the groupconsisting of hydrogen, chlorine and bromine, Y represents methyl, Arepresents a radical selected from the group consisting of hydrogen,methyl and ethyl, T represents an electron pair, and/or a salt thereof.11. The intermediate of formula (X) according to claim 10, wherein Qrepresents oxygen, W represents hydrogen, A represents methyl or ethyl.12. The intermediate of formula (X) according to claim 11, wherein Arepresents methyl.